Literature DB >> 23140505

Diastereoselective and enantioselective desymmetrization of α-substituted cyclohexadienones via intramolecular Stetter reaction.

Min-Qiang Jia1, Chuan Liu, Shu-Li You.   

Abstract

Highly diastereoselective and enantioselective desymmetrization of α-substituted cyclohexadienones via NHC-catalyzed intramolecular Stetter reaction was realized. Amino-indanol derived triazolium salt bearing a C(6)F(5) group was found to be the optimal catalyst precursor in the intramolecular Stetter reaction furnishing tricyclic products bearing multi-stereocenters in up to 96% yield and >99% ee.

Entities:  

Year:  2012        PMID： 23140505     DOI： 10.1021/jo3022555

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


  8 in total

1.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

2.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

3.  Asymmetric transformations of achiral 2,5-cyclohexadienones.

Authors:  Kyle A Kalstabakken; Andrew M Harned
Journal:  Tetrahedron       Date:  2014-12-23       Impact factor: 2.457

4.  Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application.

Authors:  Daniel T Cohen; Ryne C Johnston; Nicholas T Rosson; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-14       Impact factor: 6.222

Review 5.  Acyclic Twisted Amides.

Authors:  Guangrong Meng; Jin Zhang; Michal Szostak
Journal:  Chem Rev       Date:  2021-08-18       Impact factor: 72.087

6.  Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition.

Authors:  Matthew A Horwitz; Elisabetta Massolo; Jeffrey S Johnson
Journal:  Beilstein J Org Chem       Date:  2017-04-24       Impact factor: 2.883

7.  Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut-Currier reaction of allenoates.

Authors:  Weijun Yao; Xiaowei Dou; Shan Wen; Ji'en Wu; Jagadese J Vittal; Yixin Lu
Journal:  Nat Commun       Date:  2016-10-04       Impact factor: 14.919

8.  Organocatalytic asymmetric chlorinative dearomatization of naphthols.

Authors:  Qin Yin; Shou-Guo Wang; Xiao-Wei Liang; De-Wei Gao; Jun Zheng; Shu-Li You
Journal:  Chem Sci       Date:  2015-04-27       Impact factor: 9.825
  8 in total

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