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Search for "organozinc" in Full Text gives 54 result(s) in Beilstein Journal of Organic Chemistry.
Recent progress on the total synthesis of acetogenins from Annonaceae
- Nianguang Li,
- Zhihao Shi,
- Yuping Tang,
- Jianwei Chen and
- Xiang Li
Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48
- stereoselective addition of the organozinc reagent 305 to aldehyde 304. The ester 308 was condensed with the TBS ether of (S)-lactic aldehyde 309 to afford the γ-lactone adduct 310. Exposure of the alcohol 310 to trifluoroacetic anhydride and triethylamine led to the triol 300a. 10(S)-Asimin (300b) was prepared
- from aldehyde 304 by an identical sequence, using the enantiomer of 306 in the addition of the organozinc reagent. By comparing the MTPA ester of diastereomeric alcohols 300a and 300b with the authentic MTPA ester, the stereochemistry at C-10 of asimin (300) assigned as R. Total synthesis of bullatacin
Graphical Abstract
Scheme 1: Total synthesis of longifolicin by Marshall’s group.
Scheme 2: Total synthesis of corossoline by Tanaka’s group.
Scheme 3: Total synthesis of corossoline by Wu’s group.
Scheme 4: Total synthesis of pseudo-annonacin A by Hanessian’s group.
Scheme 5: Total synthesis of tonkinecin by Wu’s group.
Scheme 6: Total synthesis of gigantetrocin A by Shi’s group.
Scheme 7: Total synthesis of annonacin by Wu’s group.
Scheme 8: Total synthesis of solamin by Kitahara’s group.
Scheme 9: Total synthesis of solamin by Mioskowski’s group.
Scheme 10: Total synthesis of cis-solamin by Makabe’s group.
Scheme 11: Total synthesis of cis-solamin by Brown’s group.
Scheme 12: The formal synthesis of (+)-cis-solamin by Donohoe’s group.
Scheme 13: Total synthesis of cis-solamin by Stark’s group.
Scheme 14: Total synthesis of mosin B by Tanaka’s group.
Scheme 15: Total synthesis of longicin by Hanessian’s group.
Scheme 16: Total synthesis of murisolin and 16,19-cis-murisolin by Tanaka’s group.
Scheme 17: Synthesis of a stereoisomer library of (+)-murisolin by Curran’s group.
Scheme 18: Total synthesis of murisolin by Makabe’s group.
Scheme 19: Total synthesis of reticulatain-1 by Makabe’s group.
Scheme 20: Total synthesis of muricatetrocin C by Ley’s group.
Scheme 21: Total synthesis of (4R,12S,15S,16S,19R,20R,34S)-muricatetrocin (146) and (4R,12R,15S,16S,19R,20R,34S...
Scheme 22: Total synthesis of parviflorin by Hoye’s group.
Scheme 23: Total synthesis of parviflorin by Trost’s group.
Scheme 24: Total synthesis of trilobacin by Sinha’s group.
Scheme 25: Total synthesis of 15-epi-annonin I 181b by Scharf’s group.
Scheme 26: Total synthesis of squamocin A and squamocin D by Scharf’s group.
Scheme 27: Total synthesis of asiminocin by Marshall’s group.
Scheme 28: Total synthesis of asiminecin by Marshall’s group.
Scheme 29: Total synthesis of (+)-(30S)-bullanin by Marshall’s group.
Scheme 30: Total synthesis of uvaricin by the group of Sinha and Keinan.
Scheme 31: Formal synthesis of uvaricin by Burke’s group.
Scheme 32: Total synthesis of trilobin by Marshall’s group.
Scheme 33: Total synthesis of trilobin by the group of Sinha and Keinan.
Scheme 34: Total synthesis of asimilobin by the group of Wang and Shi.
Scheme 35: Total synthesis of squamotacin by the group of Sinha and Keinan.
Scheme 36: Total synthesis of asimicin by Marshall’s group.
Scheme 37: Total synthesis of asimicin by the group of Sinha and Keinan.
Scheme 38: Total synthesis of asimicin by Roush’s group.
Scheme 39: Total synthesis of asimicin by Marshall’s group.
Scheme 40: Total synthesis of 10-hydroxyasimicin by Ley’s group.
Scheme 41: Total synthesis of asimin by Marshall’s group.
Scheme 42: Total synthesis of bullatacin by the group of Sinha and Keinan.
Scheme 43: Total synthesis of bullatacin by Roush’s group.
Scheme 44: Total synthesis of bullatacin by Pagenkopf’s group.
Scheme 45: Total synthesis of rollidecins C and D by the group of Sinha and Keinan.
Scheme 46: Total synthesis of 30(S)-hydroxybullatacin by Marshall’s group.
Scheme 47: Total synthesis of uvarigrandin A and 5(R)-uvarigrandin A by Marshall’s group.
Scheme 48: Total synthesis of membranacin by Brown’s group.
Scheme 49: Total synthesis of membranacin by Lee’s group.
Scheme 50: Total synthesis of rolliniastatin 1 and rollimembrin by Lee’s group.
Scheme 51: Total synthesis of longimicin D by the group of Maezaki and Tanaka.
Scheme 52: Total synthesis of the structure proposed for mucoxin by Borhan’s group.
Scheme 53: Modular synthesis of adjacent bis-THF annonaceous acetogenins by Marshall’s group.
Scheme 54: Total synthesis of 4-deoxygigantecin by Tanaka’s group.
Scheme 55: Total synthesis of squamostatins D by Marshall’s group.
Scheme 56: Total synthesis of gigantecin by Crimmins’s group.
Scheme 57: Total synthesis of gigantecin by Hoye’s group.
Scheme 58: Total synthesis of cis-sylvaticin by Donohoe’s group.
Scheme 59: Total synthesis of 17(S),18(S)-goniocin by Sinha’s group.
Scheme 60: Total synthesis of goniocin and cyclogoniodenin T by the group of Sinha and Keinan.
Scheme 61: Total synthesis of jimenezin by Takahashi’s group.
Scheme 62: Total synthesis of jimenezin by Lee’s group.
Scheme 63: Total synthesis of jimenezin by Hoffmann’s group.
Scheme 64: Total synthesis of muconin by Jacobsen’s group.
Scheme 65: Total synthesis of (+)-muconin by Kitahara’s group.
Scheme 66: Total synthesis of muconin by Takahashi’s group.
Scheme 67: Total synthesis of muconin by the group of Yoshimitsu and Nagaoka.
Scheme 68: Total synthesis of mucocin by the group of Sinha and Keinan.
Scheme 69: Total synthesis of mucocin by Takahashi’s group.
Scheme 70: Total synthesis of (−)-mucocin by Koert’s group.
Scheme 71: Total synthesis of mucocin by the group of Takahashi and Nakata.
Scheme 72: Total synthesis of mucocin by Evans’s group.
Scheme 73: Total synthesis of mucocin by Mootoo’s group.
Scheme 74: Total synthesis of (−)-mucocin by Crimmins’s group.
Scheme 75: Total synthesis of pyranicin by the group of Takahashi and Nakata.
Scheme 76: Total synthesis of pyranicin by Rein’s group.
Scheme 77: Total synthesis of proposed pyragonicin by the group of Takahashi and Nakata.
Scheme 78: Total synthesis of pyragonicin by Rein’s group.
Scheme 79: Total synthesis of pyragonicin by Takahashi’s group.
Scheme 80: Total synthesis of squamostanal A by Figadère’s group.
Scheme 81: Total synthesis of diepomuricanin by Tanaka’s group.
Scheme 82: Total synthesis of (−)-muricatacin [(R,R)-373a] and its enantiomer (+)-muricatacin [(S,S)-373b] by ...
Scheme 83: Total synthesis of epi-muricatacin (+)-(S,R)-373c and (−)-(R,S)-373d by Scharf’s group.
Scheme 84: Total synthesis of (−)-muricatacin 373a and 5-epi-(−)-muricatacin 373d by Uang’s group.
Scheme 85: Total synthesis of four stereoisomers of muricatacin by Yoon’s group.
Scheme 86: Total synthesis of (+)-muricatacin by Figadère’s group.
Scheme 87: Total synthesis of (+)-epi-muricatacin and (−)-muricatacin by Couladouros’s group.
Scheme 88: Total synthesis of muricatacin by Trost’s group.
Scheme 89: Total synthesis of (−)-(4R,5R)-muricatacin by Heck and Mioskowski’s group.
Scheme 90: Total synthesis of muricatacin (−)-373a by the group of Carda and Marco.
Scheme 91: Total synthesis of (−)- and (+)-muricatacin by Popsavin’s group.
Scheme 92: Total synthesis of (−)-muricatacin by the group of Bernard and Piras.
Scheme 93: Total synthesis of (−)-muricatacin by the group of Yoshimitsu and Nagaoka.
Scheme 94: Total synthesis of (−)-muricatacin by Quinn’s group.
Scheme 95: Total synthesis of montecristin by Brückner’s group.
Scheme 96: Total synthesis of (−)-acaterin by the group of Franck and Figadère.
Scheme 97: Total synthesis of (−)-acaterin by Singh’s group.
Scheme 98: Total synthesis of (−)-acaterin by Kumar’s group.
Scheme 99: Total synthesis of rollicosin by Quinn’s group.
Scheme 100: Total synthesis of Rollicosin by Makabe’s group.
Scheme 101: Total synthesis of squamostolide by Makabe’s group.
Scheme 102: Total synthesis of tonkinelin by Makabe’s group.
Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C2- symmetric diols
- Y. Alpagut,
- B. Goldfuss and
- J.-M. Neudörfl
Beilstein J. Org. Chem. 2008, 4, No. 25, doi:10.3762/bjoc.4.25
- enantioselective organozinc catalysts [14][15][16][17][18], in chiral n-butyllithium aggregates [19][20][21][22][23] and in enantioselective Pd- and Cu-catalyzed C-C-couplings [9][10][24]. Here we present syntheses and characterizations of new enantiopure C2-symmetric diols based on (−)-menthone, (−)-verbenone and
Graphical Abstract
Scheme 1: Atropisomeric BINOL and conformationally restricted, (−)-fenchone-based (M)-BIFOL.
Scheme 2: Syntheses of (M)-BIMOL, (P)-BIVOL, (P)-BICOL, and (P)-BIMEOL.
Figure 1: X-Ray crystal structure of (M)-BIMOL. An acetone molecule, binding to the external OH group, is omi...
Figure 2: X-Ray crystal structure of (P)-BIVOL. A water molecule, binding to the external OH group, is omitte...
Figure 3: X-Ray crystal structure of (P)-BICOL. A water molecule, binding to the external OH group, is omitte...
Figure 4: X-Ray crystal structure of (P)-BIMEOL. An ethanol molecule, binding to the external OH group, is om...
Figure 5: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIMOL, Erel. = 0.0 kcal/mol.
Figure 6: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIMOL, Erel. = 1.3 kcal/mol.
Figure 7: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIVOL, Erel. = 5.1 kcal/mol.
Figure 8: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIVOL, Erel. = 0.0 kcal/mol.
Figure 9: B3LYP/6-31++G**:AM1 optimized structure of (M)-BICOL, Erel. = 5.8 kcal/mol.
Figure 10: B3LYP/6-31++G**:AM1 optimized structure of (P)-BICOL, Erel. = 0.0 kcal/mol.
Figure 11: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIMEOL, Erel. = 5.4 kcal/mol.
Figure 12: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIMEOL, Erel. = 0.0 kcal/mol.
Scheme 3: Co-solvent adducts in the X-ray structures of (M)-BIMOL, (P)-BIVOL, (P)-BICOL, and (P)-BIMEOL.
A superior P-H phosphonite: Asymmetric allylic substitutions with fenchol- based palladium catalysts
- Bernd Goldfuss,
- Thomas Löschmann,
- Tina Kop-Weiershausen,
- Jörg Neudörfl and
- Frank Rominger
Beilstein J. Org. Chem. 2006, 2, No. 7, doi:10.1186/1860-5397-2-7
- Leeuwen's bulky, monodentate TADDOL based phosphoramidite gave rise to intriguing memory effects [28b] and yielded 6% branched product with 25% ee (Scheme 2) [9]. We have recently employed modular, chelating fencholates, [10][11][12][13][14] in enantioselective organozinc catalysts, [15][16][17][18][19] and
Graphical Abstract
Scheme 1: Pd-catalyzed allylic substitution with unsymmetrical substrates (Nu = dimethylmalonate, Nf = OAc).
Scheme 2: Bidentate P, N-ligands and a monodentate phosphoramidite for Pd-catalyzed allylic substitutions wit...
Scheme 3: Fenchole-based phosphorus ligands (i.e. FEENOPs and BIFOPs) for Pd-catalyzed allylic substitutions....
Scheme 4: Allylic alkylation of 1-phenyl-2-propenyl acetate by sodium dimethylmalonate (BSA-method) with Pd-F...
Figure 1: X-ray crystal structure of the cationic complex Pd-FENOP (CCDC 299944), the perchlorate counterion ...
Figure 2: X-ray crystal structure of the cationic complex Pd-FENOP-Me (CCDC 600369), the perchlorate counteri...
Figure 3: X-ray crystal structure of the cationic complex Pd-FENOP-NMe2 (CCDC 600370), the perchlorate counte...
Figure 4: The two most stable ONIOM(B3LYP/SDD(+ECP) (Pd) /6-31G* (C, H, O, N, P) : UFF) optimized transition ...
Figure 5: The two most stable ONIOM(B3LYP/SDD(+ECP) (Pd) /6-31G* (C, H, O, N, P) : UFF) optimized transition ...
An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions
- T. Kop-Weiershausen,
- J. Lex,
- J.-M. Neudörfl and
- B. Goldfuss
Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6
- recently applied in chiral organolithium reagents [52][53][54][55][56][57][58] and in organozinc [59][60][61][62] as well as in organopalladium catalysts [63][64][65][66][67] to study origins of enantioselectivities in C-C-couplings. The rigid, terpene-based bicyclo[2.2.1]heptane unit enables efficient
Graphical Abstract
Scheme 1: Monodentate phosphorus ligands, e.g. BINOL-based phosphoramidites or TADDOL-based phosphites, are h...
Scheme 2: Modular phosphoramidites (R= NR'2) or phosphites (R= OR') from reactive chlorophosphite intermediat...
Figure 1: X-ray crystal structure of BIFOP-Cl (1). Distances are given in Å. (BAA = biaryl angle between C2-C1...
Figure 2: X-ray structures of BIFOP-Br (2). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'-C2...
Scheme 3: Synthesis of biphenyl-2,2'-bisfenchol (BIFOL) based phosphane derivatives (BIFOPs).
Figure 3: X-ray structures of BIFOP-H (3). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'-C2...
Figure 4: X-ray structures of BIFOP-nBu (5). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'-C...
Figure 5: X-ray structures of BIFOP(O)-H (8). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'...
Figure 6: X-ray structures of phosphite BIFOP-OPh (6). Distances are given in Å. (BAA = biaryl angle between C...
Figure 7: X-ray structures of phosphoramidite BIFOP-NEt2 (7). Distances are given in Å. (BAA = biaryl angle b...
Figure 8: X-ray structures of BIFOP(O)-Cl (9). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1...
Scheme 4: Geometries of BIFOP-systems with respect to biaryl dihedral angles (C2-C1-C1’-C2’, BAA), fenchyl-ar...
Figure 9: Computed geometry (PM3) of plus-(P)-BIFOP-Cl with unnatural plus-(P)-biaryl conformation. Distances...
Scheme 5: Biphenyl-2,2'-bisfenchol based phosphanes (BIFOPs) as chiral ligands in enantioselective Cu-catalyz...
Scheme 6: Anharmonic B3LYP/6-31G*(C,H,N,O,F,Cl,Br) /SDD(Cu) CO-stretching frequencies to assess metal to liga...
