Literature DB >> 19281239

Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.

Barry M Trost1, Julien Hitce.   

Abstract

Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.

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Year:  2009        PMID： 19281239      PMCID： PMC2679032          DOI： 10.1021/ja809723u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction.

Authors:  Barry M Trost; Alec Fettes; Brock T Shireman
Journal:  J Am Chem Soc       Date:  2004-03-10       Impact factor: 15.419

2.  Asymmetric Michael addition of nitroalkanes to nitroalkenes catalyzed by C2-symmetric tridentate bis(oxazoline) and bis(thiazoline) zinc complexes.

Authors:  Shao-Feng Lu; Da-Ming Du; Jiaxi Xu; Shi-Wei Zhang
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

3.  Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram.

Authors:  David M Barnes; Jianguo Ji; Michael G Fickes; Michael A Fitzgerald; Steven A King; Howard E Morton; Frederick A Plagge; Margo Preskill; Seble H Wagaw; Steven J Wittenberger; Ji Zhang
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

4.  Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids.

Authors:  Dong Xue; Ying-Chun Chen; Qi-Wei Wang; Ling-Feng Cun; Jin Zhu; Jin-Gen Deng
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

5.  Scope and mechanism of enantioselective Michael additions of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by nickel(II)-diamine complexes.

Authors:  David A Evans; Shizue Mito; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2007-08-24       Impact factor: 15.419

6.  Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis.

Authors:  Akitake Yamaguchi; Shigeki Matsunaga; Masakatsu Shibasaki
Journal:  Org Lett       Date:  2008-05-07       Impact factor: 6.005

7.  Exploiting orthogonally reactive functionality: synthesis and stereochemical assignment of (-)-ushikulide A.

Authors:  Barry M Trost; Brendan M O'Boyle
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

8.  Catalytic enantioselective Michael addition of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by well-defined chiral ru amido complexes.

Authors:  Masahito Watanabe; Ayako Ikagawa; Hui Wang; Kunihiko Murata; Takao Ikariya
Journal:  J Am Chem Soc       Date:  2004-09-15       Impact factor: 15.419

9.  Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks.

Authors:  Barry M Trost; Sushant Malhotra; Takashi Mino; Naomi S Rajapaksa
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Catalytic asymmetric vinylogous mannich reaction of N-(2-thienyl)sulfonylimines.

Authors:  Alvaro Salvador González; Ramón Gómez Arrayás; Marta Rodríguez Rivero; Juan C Carretero
Journal:  Org Lett       Date:  2008-09-09       Impact factor: 6.005
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  10 in total

1.  Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates.

Authors:  Xinfang Xu; Wen-Hao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-31       Impact factor: 15.336

2.  Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis.

Authors:  Giorgio Bencivenni; Patrizia Galzerano; Andrea Mazzanti; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Proc Natl Acad Sci U S A       Date:  2010-06-21       Impact factor: 11.205

3.  Enantioselective ProPhenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products.

Authors:  Barry M Trost; Vincent S Chan; Daisuke Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

4.  Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

Review 5.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

6.  Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Org Lett       Date:  2012-02-22       Impact factor: 6.005

7.  Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors:  Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal:  Chemistry       Date:  2012-10-23       Impact factor: 5.236

8.  An efficient and facile synthesis of 3-amino-5-chromenyl-butenolides from 3-formyl chromone, dialkyl acetylenedicarboxylate, and primary amines.

Authors:  Saeed Balalaie; Morteza Ashouriha; Frank Rominger; Hamid Reza Bijanzadeh
Journal:  Mol Divers       Date:  2013-01-23       Impact factor: 2.943

9.  Characterization of stereoisomeric 5-(2-nitro-1-phenylethyl)furan-2(5H)-ones by computation of 1 H and 13 C NMR chemical shifts and electronic circular dichroism spectra.

Authors:  Dayane T Lopes; Thomas R Hoye; Elson S Alvarenga
Journal:  Magn Reson Chem       Date:  2020-07-15       Impact factor: 2.447

10.  Lewis acid-catalyzed asymmetric reactions of β,γ-unsaturated 2-acyl imidazoles.

Authors:  Tengfei Kang; Liuzhen Hou; Sai Ruan; Weidi Cao; Xiaohua Liu; Xiaoming Feng
Journal:  Nat Commun       Date:  2020-08-03       Impact factor: 14.919
  10 in total

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