Literature DB >> 21520898

Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids.

Chong Kiat Tan1, Ling Zhou, Ying-Yeung Yeung.   

Abstract

An efficient and enantioselective bromolactonization of 1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst has been developed, resulting in the formation of δ-lactones containing two chiral centers with up to 99% yield, 95% ee.

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Year:  2011        PMID： 21520898     DOI： 10.1021/ol200840e

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


  11 in total

1.  Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Org Lett       Date:  2011-12-06       Impact factor: 6.005

2.  Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds.

Authors:  Daniel H Paull; Chao Fang; James R Donald; Andrew D Pansick; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2012-06-27       Impact factor: 15.419

3.  Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.

Authors:  Jeremy D Griffin; Cortney L Cavanaugh; David A Nicewicz
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-20       Impact factor: 15.336

4.  Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Chirality       Date:  2013-11-07       Impact factor: 2.437

5.  A photo-Favorskii ring contraction reaction: the effect of ring size.

Authors:  Viju Balachandran Kammath; Tomáš Šolomek; Bokolombe Pitchou Ngoy; Dominik Heger; Petr Klán; Marina Rubina; Richard S Givens
Journal:  J Org Chem       Date:  2012-06-19       Impact factor: 4.354

Review 6.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

7.  Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

8.  Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors:  Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal:  J Org Chem       Date:  2018-05-22       Impact factor: 4.354

9.  Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst.

Authors:  Chao Fang; Daniel H Paull; J Caleb Hethcox; Christopher R Shugrue; Stephen F Martin
Journal:  Org Lett       Date:  2012-11-30       Impact factor: 6.005

10.  Toward Catalytic, Enantioselective Chlorolactonization of 1,2-Disubstituted Styrenyl Carboxylic Acids.

Authors:  Scott E Denmark; Pavel Ryabchuk; Matthew T Burk; Bradley B Gilbert
Journal:  J Org Chem       Date:  2016-08-24       Impact factor: 4.354
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