Literature DB >> 14572288

Addition of Bu3SnLi to tert-butanesulfinimines as an efficient route to chiral, nonracemic alpha-aminoorganostannanes.

Kevin W Kells1, J Michael Chong.   

Abstract

[reaction: see text]. Addition of Bu3SnLi to tert-butanesulfinimines proceeds with high diastereoselectivities to provide the expected adducts in excellent yields and typically with dr = >99:1. These adducts are readily converted to enantiomerically enriched N-Boc-protected alpha-aminoorganostannanes with complete retention of configuration.

Entities:  

Year:  2003        PMID: 14572288     DOI: 10.1021/ol035702i

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


  3 in total

1.  Expedient synthesis of sulfinamides from sulfonyl chlorides.

Authors:  Michael Harmata; Pinguan Zheng; Chaofeng Huang; Maria G Gomes; Weijiang Ying; Kanok-On Rayanil; Kanok-On Ranyanil; Gayatri Balan; Nathan L Calkins
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

2.  Overview of Carbanion Dynamics and Electrophilic Substitutions in Chiral Organolithium Compounds.

Authors:  Robert E Gawley
Journal:  Top Stereochem       Date:  2010-01-01

3.  A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters.

Authors:  Xinghua Ma; Haoran Zhao; Meruyert Binayeva; Glenn Ralph; Mohamed Diane; Shibin Zhao; Chao-Yuan Wang; Mark R Biscoe
Journal:  Chem       Date:  2020-03-02       Impact factor: 22.804

  3 in total

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