Literature DB >> 19265416

Highly regio- and stereoselective oxidative hydroacetoxylation of 1,2-allenylic sulfoxides via a different mechanism.

Chao Zhou1, Zhao Fang, Chunling Fu, Shengming Ma.   

Abstract

A highly regio- and stereoselective oxidative hydroacetoxylation of 1,2-allenylic sulfoxides affording 1-sulfonyl-1-alken-3-yl acetates in moderate to good yields was developed. Through the X-ray diffraction study, it was observed that the reaction may proceed via a 5-membered cyclic intermediate and the (-)OAc attacks the chiral carbon atom, which is different from what was observed in our previous study.

Entities:  

Year:  2009        PMID: 19265416     DOI: 10.1021/jo802755k

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


  1 in total

1.  Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Brønsted acids. NMR and DFT study of these cations and their reactions.

Authors:  Stanislav V Lozovskiy; Alexander Yu Ivanov; Olesya V Khoroshilova; Aleksander V Vasilyev
Journal:  Beilstein J Org Chem       Date:  2018-11-22       Impact factor: 2.883

  1 in total

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