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Search for "BINOL phosphate" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.
Group 13 exchange and transborylation in catalysis
- Dominic R. Willcox and
- Stephen P. Thomas
Beilstein J. Org. Chem. 2023, 19, 325–348, doi:10.3762/bjoc.19.28
- achieved. When AgOTf was replaced with silver (R)-BINOL phosphate, the asymmetric allylation proceeded in a moderate yield (60%) and enantioselectivity (40% ee). The structure of the ‘GaIOTf’ species was explored in more detail by Slattery, and a monovalent [GaI(18-crown-6)OTf] complex was isolated and
Graphical Abstract
Scheme 1: Group 13 exchange.
Scheme 2: Borane-catalysed hydroboration of alkynes and the proposed mechanism.
Scheme 3: a) Borane-catalysed hydroboration of alkenes and the proposed mechanism. b) H-B-9-BBN-catalysed dou...
Scheme 4: a) Amine-borane-catalysed C‒H borylation of heterocycles and the proposed mechanism. b) Benzoic aci...
Scheme 5: Bis(pentafluorophenyl)borane-catalysed dimerisation of allenes and the proposed mechanism.
Scheme 6: Alkoxide-promoted hydroboration of heterocycles and the proposed mechanism.
Scheme 7: Borane-catalysed reduction of indoles and the proposed mechanism.
Scheme 8: H-B-9-BBN-catalysed hydrocyanation of enones and the proposed mechanism.
Scheme 9: Borane-catalysed hydroboration of nitriles and the proposed mechanism.
Scheme 10: Myrtanylborane-catalysed asymmetric reduction of propargylic ketones and the proposed mechanism.
Scheme 11: H-B-9-BBN-catalysed C–F esterification of alkyl fluorides and the proposed mechanism.
Scheme 12: H-B-9-BBN-catalysed 1,4-hydroboration of enones and the proposed mechanism.
Scheme 13: Boric acid-promoted reduction of esters, lactones, and carbonates and the proposed mechanism.
Scheme 14: H-B-9-BBN-catalysed reductive aldol-type reaction and the proposed mechanism.
Scheme 15: H-B-9-BBN-catalysed diastereoselective allylation of ketones and the Ph-BBD-catalysed enantioselect...
Scheme 16: H-B-9-BBN-catalysed C–F arylation of benzyl fluorides and the proposed mechanism.
Scheme 17: Borane-catalysed S‒H borylation of thiols and the proposed mechanism.
Scheme 18: Borane-catalysed hydroalumination of alkenes and allenes.
Scheme 19: a) Aluminium-catalysed hydroboration of alkynes and example catalysts. b) Deprotonation mechanistic...
Scheme 20: Aluminium-catalysed hydroboration of alkenes and the proposed mechanism.
Scheme 21: Aluminium-catalysed C–H borylation of terminal alkynes and the proposed mechanism.
Scheme 22: Aluminium-catalysed dehydrocoupling of amines, alcohols, and thiols with H-B-9-BBN or HBpin and the...
Scheme 23: Aluminium-catalysed hydroboration of unsaturated compounds and the general reaction mechanism.
Scheme 24: a) Gallium-catalysed asymmetric hydroboration of ketones and the proposed mechanism. b) Gallium-cat...
Scheme 25: Gallium(I)-catalysed allylation/propargylation of acetals and aminals and the proposed mechanism.
Scheme 26: Indium(I)-catalysed allylation/propargylation of acetals, aminals, and alkyl ethers.
Scheme 27: Iron–indium cocatalysed double hydroboration of nitriles and the proposed mechanism.
Figure 1: a) The number of reports for a given group 13 exchange in catalysis. b) Average free energy barrier...
β-Hydroxy sulfides and their syntheses
- Mokgethwa B. Marakalala,
- Edwin M. Mmutlane and
- Henok H. Kinfe
Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143
- ranged from –78 °C to room temperature. The use of amines, alcohols as well as alkyl and arylthiols as nucleophiles failed to provide the corresponding products. A year later, Antilla and co-workers found lithium-binol phosphate 64 to be an efficient catalyst for the desymmetrization of meso-epoxides
- complex. Enantioselective ring-opening reaction of stilbene oxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol–titanium complex. Asymmetric desymmetrization of meso-epoxides using BINOL-based Brønsted acid catalysts. Lithium-BINOL-phosphate-catalyzed desymmetrization of meso-epoxides with
Graphical Abstract
Figure 1: Some sulfur-containing natural products.
Figure 2: Some natural products incorporating β-hydroxy sulfide moieties.
Figure 3: Some synthetic β-hydroxy sulfides of clinical value.
Scheme 1: Alumina-mediated synthesis of β-hydroxy sulfides, ethers, amines and selenides from epoxides.
Scheme 2: β-Hydroxy sulfide syntheses by ring opening of epoxides under different Lewis and Brønsted acid and...
Scheme 3: n-Bu3P-catalyzed thiolysis of epoxides and aziridines to provide the corresponding β-hydroxy and β-...
Scheme 4: Zinc(II) chloride-mediated thiolysis of epoxides.
Scheme 5: Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides under microwave irradiation.
Scheme 6: Gallium triflate-catalyzed ring opening of epoxides and one-pot oxidation.
Scheme 7: Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides using Ga(OTf)3 as a catalyst.
Scheme 8: Ring opening of epoxide using ionic liquids under solvent-free conditions.
Scheme 9: N-Bromosuccinimide-catalyzed ring opening of epoxides.
Scheme 10: LiNTf2-mediated epoxide opening by thiophenol.
Scheme 11: Asymmetric ring-opening of cyclohexene oxide with various thiols catalyzed by zinc L-tartrate.
Scheme 12: Catalytic asymmetric ring opening of symmetrical epoxides with t-BuSH catalyzed by (R)-GaLB (43) wi...
Scheme 13: Asymmetric ring opening of meso-epoxides by p-xylenedithiol catalyzed by a (S,S)-(salen)Cr complex.
Scheme 14: Desymmetrization of meso-epoxide with thiophenol derivatives.
Scheme 15: Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chira...
Scheme 16: Enantioselective ring-opening reaction of stilbene oxides with ArSH catalyzed by a C2-symmetric chi...
Scheme 17: Asymmetric desymmetrization of meso-epoxides using BINOL-based Brønsted acid catalysts.
Scheme 18: Lithium-BINOL-phosphate-catalyzed desymmetrization of meso-epoxides with aromatic thiols.
Scheme 19: Ring-opening reactions of cyclohexene oxide with thiols by using CPs 1-Eu and 2-Tb.
Scheme 20: CBS-oxazaborolidine-catalyzed borane reduction of β-keto sulfides.
Scheme 21: Preparation of β-hydroxy sulfides via connectivity.
Scheme 22: Baker’s yeast-catalyzed reduction of sulfenylated β-ketoesters.
Scheme 23: Sodium-mediated ring opening of epoxides.
Scheme 24: Disulfide bond cleavage-epoxide opening assisted by tetrathiomolybdate.
Scheme 25: Proposed reaction mechanism of disulfide bond cleavage-epoxide opening assisted by tetrathiomolybda...
Scheme 26: Cyclodextrin-catalyzed difunctionalization of alkenes.
Scheme 27: Zinc-catalyzed synthesis of β-hydroxy sulfides from disulfides and alkenes.
Scheme 28: tert-Butyl hydroperoxide-catalyzed hydroxysulfurization of alkenes.
Scheme 29: Proposed mechanism of the radical hydroxysulfurization.
Scheme 30: Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfides.
Scheme 31: Proposed mechanism of Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfid...
Scheme 32: Copper(II)-catalyzed synthesis of β-hydroxy sulfides 15e,f from alkenes and basic disulfides.
Scheme 33: CuI-catalyzed acetoxysulfenylation of alkenes.
Scheme 34: CuI-catalyzed acetoxysulfenylation reaction mechanism.
Scheme 35: One-pot oxidative 1,2-acetoxysulfenylation of Baylis–Hillman products.
Scheme 36: Proposed mechanism for the oxidative 1,2-acetoxysulfination of Baylis–Hillman products.
Scheme 37: 1,2-Acetoxysulfenylation of alkenes using DIB/KI.
Scheme 38: Proposed reaction mechanism of the diacetoxyiodobenzene (DIB) and KI-mediated 1,2-acetoxysulfenylat...
Scheme 39: Catalytic asymmetric thiofunctionalization of unactivated alkenes.
Scheme 40: Proposed catalytic cycle for asymmetric sulfenofunctionalization.
Scheme 41: Synthesis of thiosugars using intramolecular thiol-ene reaction.
Scheme 42: Synthesis of leukotriene C-1 by Corey et al.: (a) N-(trifluoroacetyl)glutathione dimethyl ester (3 ...
Scheme 43: Synthesis of pteriatoxins with epoxide thiolysis to attain β-hydroxy sulfides. Reagents: (a) (1) K2...
Scheme 44: Synthesis of peptides containing a β-hydroxy sulfide moiety.
Scheme 45: Synthesis of diltiazem (12) using biocatalytic resolution of an epoxide followed by thiolysis.
Asymmetric Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene
- Magnus Rueping and
- Sadiya Raja
Beilstein J. Org. Chem. 2012, 8, 1819–1824, doi:10.3762/bjoc.8.208
- optically active aza-tetracycles in good yields with high diastereo- and enantioselectivities under mild reaction conditions. Keywords: BINOL phosphate; [4 + 2] cycloaddition; Diels–Alder reaction; organocatalysis; Introduction The enantioselective aza-Diels–Alder reaction is an important method for the
Graphical Abstract
Scheme 1: Brønsted acid catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene.
