Literature DB >> 20945837

Asymmetric bromolactonization using amino-thiocarbamate catalyst.

Ling Zhou1, Chong Kiat Tan, Xiaojian Jiang, Feng Chen, Ying-Yeung Yeung.   

Abstract

A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

Entities:  

Year:  2010        PMID: 20945837     DOI: 10.1021/ja1048972

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


  29 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.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

4.  Biomimetic Desymmetrization of a Carboxylic Acid.

Authors:  Matthew T Knowe; Michael W Danneman; Sarah Sun; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-02-05       Impact factor: 15.419

5.  Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

Authors:  Frederick J Seidl; Chang Min; Jovan A Lopez; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419

6.  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

7.  Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

Authors:  Cheyenne S Brindle; Charles S Yeung; Eric N Jacobsen
Journal:  Chem Sci J       Date:  2013-05-01

8.  Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Authors:  Michael T Bovino; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-05       Impact factor: 15.336

9.  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

Review 10.  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

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