| Literature DB >> 17134296 |
Julia L Shamshina1, Timothy S Snowden.
Abstract
The reaction of alkenyl trichloromethyl carbinols with various nucleophiles under protic basic conditions reveals that mercaptans participate by alpha-substitution (S(N)2) of the intermediate alkenyl gem-dichloroepoxides. Conversely, hydroxide results in preferential gamma-substitution with stereoselective allylic transposition (S(N)2'). Regioselectivity with alkoxides depends upon the level of alkene substitution. [reaction: see text]Entities:
Year: 2006 PMID： 17134296 DOI： 10.1021/ol0625132
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005