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Synthesis of Enantiopure 1,5‐Enynes and 1,5‐Diynes with Propargylic Quaternary Centers
Author(s) -
Pérez Ignacio,
Yuste Francisco,
SánchezObregón Rubén,
Toscano Rubén A.,
Alemán José,
Marzo Leyre,
Martín Castro Ana M.,
Alonso Inés,
García Ruano José Luis
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500004
Subject(s) - enantiopure drug , chemistry , carbanion , allylic rearrangement , halide , stereoselectivity , quaternary carbon , stereochemistry , medicinal chemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
Diastereoselective quaternization of ortho ‐sulfinylbenzyl‐methylpropargylic carbanions has been carried out with various allylic, propargylic, and benzylic halides. The stereoselectivity is efficiently controlled by the sulfinyl group, acting as a remote chiral auxiliary. Desulfinylation of the resulting compounds with t BuLi provides access to enantiopure 1,5‐enynes, 1,5‐diynes, and 4‐arylalkynes bearing all‐carbon quaternary propargylic centers.