Literature DB >> 11700126

Catalytic direct asymmetric Michael reactions: taming naked aldehyde donors.

J M Betancort1, C F Barbas.   

Abstract

[reaction--see text] Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)pyrrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantioselectivities approaching 80%. The resulting gamma-formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.

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Year:  2001        PMID: 11700126     DOI: 10.1021/ol0167006

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  17 in total

1.  A Diels-Alder Reaction Conducted Within the Parameters of Aqueous Organocatalysis: Still Just Smoke and Mirrors.

Authors:  G Neil Stowe; Kim D Janda
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors:  Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2008-04-04       Impact factor: 15.419

Review 3.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

4.  Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

Authors:  Grant S Buchanan; Huifang Dai; Richard P Hsung; Aleksey I Gerasyuto; Casi M Scheinebeck
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

5.  Organocatalytic asymmetric assembly reactions for the syntheses of carbohydrate derivatives by intermolecular Michael-Henry reactions.

Authors:  Hisatoshi Uehara; Ritsuo Imashiro; Gloria Hernández-Torres; Carlos F Barbas
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

6.  Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.

Authors:  Benjamin W Turnpenny; Sherry R Chemler
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

7.  Total synthesis of eudesmane terpenes by site-selective C-H oxidations.

Authors:  Ke Chen; Phil S Baran
Journal:  Nature       Date:  2009-05-13       Impact factor: 49.962

8.  Stereospecific synthesis of conformationally constrained gamma-amino acids: new foldamer building blocks that support helical secondary structure.

Authors:  Li Guo; Yonggui Chi; Aaron M Almeida; Ilia A Guzei; Brian K Parker; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

9.  Synthesis of Prolinal Dithioacetals as Catalysts for the Highly Stereoselective Michael Addition of Ketones and Aldehydes to beta-Nitrostyrenes.

Authors:  Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

10.  Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes.

Authors:  Jie Guang; John Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2013-10-16       Impact factor: 2.415

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