Literature DB >> 12375900

Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene.

Alexandre Alexakis1, Olivier Andrey.   

Abstract

[reaction: see text] The direct Michael addition of aldehydes and ketones to nitrostyrene, catalyzed by N-i-Pr-2,2'-bipyrrolidine, is described. The desired 1,4-adducts are obtained in excellent yield with enantioselectivities up to 85% ee and dr up to 95:5 of the syn product.

Entities:  

Year:  2002        PMID： 12375900     DOI： 10.1021/ol026543q

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


  9 in total

1.  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

2.  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

3.  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

4.  Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1(3,8)]-dodecane (TATD) towards some reducing agents: synthesis of TMEDA.

Authors:  Augusto Rivera; Jaime Rios-Motta
Journal:  Molecules       Date:  2007-07-19       Impact factor: 4.411

5.  [(1R*,2S*)-N-Benzyl-2-phenyl-1-(pyridin-2-yl)-N-(pyridin-2-ylmeth-yl)ethane-1,2-diamine]-dichloridozinc(II).

Authors:  Adailton J Bortoluzzi; Sandro L Mireski; Antonio C Joussef
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-16

6.  Catalytic enantioselective aryl transfer to aldehydes using chiral 2,2'-bispyrrolidine-based salan ligands.

Authors:  Xuefeng Jia; Aijun Lin; Zhijie Mao; Chengjian Zhu; Yixiang Cheng
Journal:  Molecules       Date:  2011-04-06       Impact factor: 4.411

7.  Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol.

Authors:  Sebastián Llopis; Teresa García; Ángel Cantín; Alexandra Velty; Urbano Díaz; Avelino Corma
Journal:  Catal Sci Technol       Date:  2018-10-23       Impact factor: 6.119

8.  NMR and Computational Studies on the Reactions of Enamines with Nitroalkenes That May Pass through Cyclobutanes.

Authors:  Alejandro Castro-Alvarez; Héctor Carneros; Jaume Calafat; Anna M Costa; Cristian Marco; Jaume Vilarrasa
Journal:  ACS Omega       Date:  2019-10-25

9.  Asymmetric Redox-Annulation of Cyclic Amines.

Authors:  YoungKu Kang; Weijie Chen; Martin Breugst; Daniel Seidel
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354
  9 in total

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