New advances in asymmetric organocatalysis
Asymmetric organocatalysis became one of the principal methods for the catalytic synthesis of chiral compounds. This thematic issue in the Beilstein Journal of Organic Chemistry aims to highlight new developments across all subdisciplines of enantioselective organocatalysis. This timely collection of articles deals with methodological advances in both covalent (enamine, iminium, phosphine, carbene, etc.) and noncovalent organocatalytic activations, which are often connected to developments of new catalysts. Important mechanistic and computational studies deepen our understanding of this topic and the underlying processes. The gradual maturation of this field is demonstrated by applications of its methodologies to target molecules synthesis, such as natural products or compounds of medicinal interest.
Submission is still open
- Letter
- Published 08 Apr 2021
-
PDF -
Album-
![]()
Graphical Abstract
-
![]()
Scheme 1: Overview about established methods to access enantioenriched 2 and the herein investigated kinetic ...
-
![]()
Scheme 2: Use of alternative acylating agents 4 for the kinetic resolution of rac-2.
-
-
Supp. Info
- Full Research Paper
- Published 14 Jun 2021
-
PDF -
Album-
![]()
Graphical Abstract
-
![]()
Scheme 1: Reactions of α-nitroketones with unsaturated pyrazolone and with 4-benzylidenepyrrolidine-2,3-dione....
-
![]()
Scheme 2: Reaction of 4-benzylidenedihydrofuran-2,3-dione (4) with α-nitroketones 2b,c. Reaction conditions: ...
-
-
Supp. Info
- Full Research Paper
- Published 21 Jul 2021
-
PDF -
Album-
![]()
Graphical Abstract
-
![]()
Scheme 1: Mechanism for the phosphine-initiated oxa-Michael addition.
-
![]()
Figure 1: Above: Michael acceptors, Michael donors and catalysts used in this study; pKa (respectively pKa of...
-
![]()
Figure 2: Left: double-bond conversion of the polymerization of 4 initiated by 5 mol % TPP, MMTPP or TMTPP af...
-
![]()
Figure 3: Left: Oxidation stability of the phosphines. Phosphine oxide content in % as determined by 31P NMR ...
-
-
Supp. Info
- Review
- Published 03 Aug 2021
-
PDF -
Album-
![]()
Graphical Abstract
-
![]()
Figure 1: Coumarin-derived commercially available drugs.
-
![]()
Figure 2: Inhibition of acetylcholinesterase by coumarin derivatives.
-
![]()
Scheme 1: Michael addition of 4-hydroxycoumarins 1 to α,β‐unsaturated enones 2.
-
![]()
Scheme 2: Organocatalytic conjugate addition of 4-hydroxycoumarin 1 to α,β-unsaturated aldehydes 2 followed b...
-
![]()
Scheme 3: Synthesis of 3,4-dihydrocoumarin derivatives 10 through decarboxylative and dearomatizative cascade...
-
![]()
Scheme 4: Total synthesis of (+)-smyrindiol (17).
-
![]()
Scheme 5: Michael addition of 4-hydroxycoumarin (1) to enones 2 through a bifunctional modified binaphthyl or...
-
![]()
Scheme 6: Michael addition of ketones 20 to 3-aroylcoumarins 19 using a cinchona alkaloid-derived primary ami...
-
![]()
Scheme 7: Enantioselective reaction of cyclopent-2-enone-derived MBH alcohols 24 with 4-hydroxycoumarins 1.
-
![]()
Scheme 8: Sequential Michael addition/hydroalkoxylation one-pot approach to annulated coumarins 28 and 30.
-
![]()
Scheme 9: Michael addition of 4-hydroxycoumarins 1 to enones 2 using a binaphthyl diamine catalyst 31.
-
![]()
Scheme 10: Asymmetric Michael addition of 4-hydroxycoumarin 1 with α,β-unsaturated ketones 2 catalyzed by a ch...
-
![]()
Scheme 11: Catalytic asymmetric β-C–H functionalization of ketones via enamine oxidation.
-
![]()
Scheme 12: Enantioselective synthesis of polycyclic coumarin derivatives 37 catalyzed by an primary amine-imin...
-
![]()
Scheme 13: Allylic alkylation reaction between 3-cyano-4-methylcoumarins 39 and MBH carbonates 40.
-
![]()
Scheme 14: Enantioselective synthesis of cyclopropa[c]coumarins 45.
-
![]()
Scheme 15: NHC-catalyzed lactonization of 2-bromoenals 46 with 4-hydroxycoumarin (1).
-
![]()
Scheme 16: NHC-catalyzed enantioselective synthesis of dihydrocoumarins 51.
-
![]()
Scheme 17: Domino reaction of enals 2 with hydroxylated malonate 53 catalyzed by NHC 55.
-
![]()
Scheme 18: Oxidative [4 + 2] cycloaddition of enals 57 to coumarins 56 catalyzed by NHC 59.
-
![]()
Scheme 19: Asymmetric [3 + 2] cycloaddition of coumarins 43 to azomethine ylides 60 organocatalyzed by quinidi...
-
![]()
Scheme 20: Synthesis of α-benzylaminocoumarins 64 through Mannich reaction between 4-hydroxycoumarins (1) and ...
-
![]()
Scheme 21: Asymmetric addition of malonic acid half-thioesters 67 to coumarins 66 using the sulphonamide organ...
-
![]()
Scheme 22: Enantioselective 1,4-addition of azadienes 71 to 3-homoacyl coumarins 70.
-
![]()
Scheme 23: Michael addition/intramolecular cyclization of 3-acylcoumarins 43 to 3-halooxindoles 74.
-
![]()
Scheme 24: Enantioselective synthesis of 3,4-dihydrocoumarins 78 catalyzed by squaramide 73.
-
![]()
Scheme 25: Organocatalyzed [4 + 2] cycloaddition between 2,4-dienals 79 and 3-coumarincarboxylates 43.
-
![]()
Scheme 26: Enantioselective one-pot Michael addition/intramolecular cyclization for the synthesis of spiro[dih...
-
![]()
Scheme 27: Michael/hemiketalization addition enantioselective of hydroxycoumarins (1) to: (a) enones 2 and (b)...
-
![]()
Scheme 28: Synthesis of 2,3-dihydrofurocoumarins 89 through Michael addition of 4-hydroxycoumarins 1 to β-nitr...
-
![]()
Scheme 29: Synthesis of pyrano[3,2-c]chromene derivatives 93 via domino reaction between 4-hydroxycoumarins (1...
-
![]()
Scheme 30: Conjugated addition of 4-hydroxycoumarins 1 to nitroolefins 95.
-
![]()
Scheme 31: Michael addition of 4-hydroxycoumarin 1 to α,β-unsaturated ketones 2 promoted by primary amine thio...
-
![]()
Scheme 32: Enantioselective synthesis of functionalized pyranocoumarins 99.
-
![]()
Scheme 33: 3-Homoacylcoumarin 70 as 1,3-dipole for enantioselective concerted [3 + 2] cycloaddition.
-
![]()
Scheme 34: Synthesis of warfarin derivatives 107 through addition of 4-hydroxycoumarins 1 to β,γ-unsaturated α...
-
![]()
Scheme 35: Asymmetric multicatalytic reaction sequence of 2-hydroxycinnamaldehydes 109 with 4-hydroxycoumarins ...
-
![]()
Scheme 36: Mannich asymmetric addition of cyanocoumarins 39 to isatin imines 112 catalyzed by the amide-phosph...
-
![]()
Scheme 37: Enantioselective total synthesis of (+)-scuteflorin A (119).
-
