Literature DB >> 20136102

Chiral bifunctional thiourea-catalyzed enantioselective Michael addition of ketones to nitrodienes.

Hai Ma1, Kun Liu, Fa-Guang Zhang, Chuan-Le Zhu, Jing Nie, Jun-An Ma.   

Abstract

Simple bifunctional thioureas, derived from the commercially available saccharides and chiral diamines, have been shown tunably to promote Michael-type addition of ketones to alpha,beta-gamma,delta-nitrodienes. The Michael adducts were obtained in good yields albeit with high enantioselectivites (84-99% ee). Furthermore, these products can be readily transformed into more useful molecules.

Entities:  

Year:  2010        PMID: 20136102     DOI: 10.1021/jo901991v

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.

Authors:  Michael R Witten; Eric N Jacobsen
Journal:  Org Lett       Date:  2015-05-08       Impact factor: 6.005

Review 2.  Synthesis and Applications of Carbohydrate-Based Organocatalysts.

Authors:  Elżbieta Wojaczyńska; Franz Steppeler; Dominika Iwan; Marie-Christine Scherrmann; Alberto Marra
Journal:  Molecules       Date:  2021-11-30       Impact factor: 4.411

3.  Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric Michael addition/reductive cyclization.

Authors:  Michael T Corbett; Qihai Xu; Jeffrey S Johnson
Journal:  Org Lett       Date:  2014-04-18       Impact factor: 6.005

Review 4.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors:  Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Molecules       Date:  2020-01-18       Impact factor: 4.411

5.  Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction.

Authors:  Alexander N Reznikov; Dmitry S Nikerov; Anastasiya E Sibiryakova; Victor B Rybakov; Evgeniy V Golovin; Yuri N Klimochkin
Journal:  Beilstein J Org Chem       Date:  2020-08-25       Impact factor: 2.883

  5 in total

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