Literature DB >> 20099813

Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl imines.

Daniel R Fandrick1, Courtney S Johnson, Keith R Fandrick, Jonathan T Reeves, Zhulin Tan, Heewon Lee, Jinhua J Song, Nathan K Yee, Chris H Senanayake.   

Abstract

A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization.

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Year:  2010        PMID： 20099813     DOI： 10.1021/ol9028258

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


  4 in total

1.  A robust, efficient, and highly enantioselective method for synthesis of homopropargyl amines.

Authors:  Erika M Vieira; Fredrik Haeffner; Marc L Snapper; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-23       Impact factor: 15.336

2.  Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.

Authors:  Barry M Trost; Dennis C Koester; Ehesan U Sharif
Journal:  Chemistry       Date:  2016-01-25       Impact factor: 5.236

3.  Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction.

Authors:  Shi-Ming Xu; Liang Wei; Chong Shen; Lu Xiao; Hai-Yan Tao; Chun-Jiang Wang
Journal:  Nat Commun       Date:  2019-12-05       Impact factor: 14.919

4.  Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

Authors:  Charlotte A Osborne; Thomas B D Endean; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2015-10-27       Impact factor: 6.005
  4 in total

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