Literature DB >> 15151433

Amine-salt-controlled, catalytic asymmetric conjugate addition of various amines and asymmetric protonation.

Yoshitaka Hamashima1, Hidenori Somei, Yuta Shimura, Toshihiro Tamura, Mikiko Sodeoka.   

Abstract

The combined use of chiral Pd complex 2 and amine salt enabled completely regulated release of free nucleophilic amine. Under these conditions, an efficient catalytic asymmetric conjugate addition of various amines was achieved to afford beta-amino acid derivatives in high chemical yields with up to 98% ee. Furthermore, a highly enantioselective protonation in 1,4-addition of amine was also developed. [reaction: see text]

Entities:  

Year:  2004        PMID: 15151433     DOI: 10.1021/ol0493711

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


  13 in total

Review 1.  Enantioselective protonation.

Authors:  Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

2.  Catalytic enantioselective stereoablative reactions: an unexploited approach to enantioselective catalysis.

Authors:  Justin T Mohr; David C Ebner; Brian M Stoltz
Journal:  Org Biomol Chem       Date:  2007-10-01       Impact factor: 3.876

3.  Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway.

Authors:  Natalia Chernyak; Serge I Gorelsky; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-07       Impact factor: 15.336

4.  Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

Authors:  Madeleine E Kieffer; Lindsay M Repka; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2012-03-05       Impact factor: 15.419

Review 5.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

6.  A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.

Authors:  Yingfu Lin; William J Hirschi; Anuj Kunadia; Anirudra Paul; Ion Ghiviriga; Khalil A Abboud; Rachael W Karugu; Mathew J Vetticatt; Jennifer S Hirschi; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2020-03-11       Impact factor: 15.419

7.  Homogeneous pd-catalyzed enantioselective decarboxylative protonation.

Authors:  Smaranda C Marinescu; Toyoki Nishimata; Justin T Mohr; Brian M Stoltz
Journal:  Org Lett       Date:  2008-02-28       Impact factor: 6.005

8.  Preparation of dicationic palladium catalysts for asymmetric catalytic reactions.

Authors:  Andrey E Sheshenev; Alexander M R Smith; King Kuok Mimi Hii
Journal:  Nat Protoc       Date:  2012-09-06       Impact factor: 13.491

9.  Rh(I)-bisphosphine-catalyzed asymmetric, intermolecular hydroheteroarylation of α-substituted acrylate derivatives.

Authors:  Claire M Filloux; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-12-29       Impact factor: 15.419

Review 10.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

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