Literature DB >> 20192183

Enantioselective bromolactonization of conjugated (Z)-enynes.

Wei Zhang1, Suqing Zheng, Na Liu, Jenny B Werness, Ilia A Guzei, Weiping Tang.   

Abstract

A catalytic enantioselective syn-1,4-bromolactonization of conjugated (Z)-enynes was reported. Diastereomeric ratios >20:1 and up to 99% enantiomeric excesses were observed. Di-, tri-, and tetra-substituted bromoallenes were prepared together with lactone heterocycles efficiently and stereoselectively. Preliminary investigations suggest that the chiral catalyst may serve as a bifunctional reagent by interacting with both a carboxylic acid nucleophile and NBS electrophile.

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Year:  2010        PMID: 20192183     DOI: 10.1021/ja100173w

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


  34 in total

1.  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

2.  Lewis base catalysis of bromo- and iodolactonization, and cycloetherification.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Proc Natl Acad Sci U S A       Date:  2010-08-12       Impact factor: 11.205

3.  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

4.  Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors:  Byunghyuck Jung; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-03       Impact factor: 15.419

5.  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

6.  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 7.  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

8.  Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions.

Authors:  Scott E Denmark; Dipannita Kalyani; William R Collins
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

9.  Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes.

Authors:  Hua-Dong Xu; Ren-Wei Zhang; Xiaoxun Li; Suyu Huang; Weiping Tang; Wen-Hao Hu
Journal:  Org Lett       Date:  2013-01-28       Impact factor: 6.005

10.  Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

Authors:  Jun-Shan Tian; Cheng-Liang Zhu; Yun-Rong Chen; Hao Xu
Journal:  Synthesis (Stuttg)       Date:  2015-06       Impact factor: 3.157

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