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Complete Regio‐ and Stereoselectivity Control in the Halohydroxylation of Non‐activated Allenes Mediated by a Remote Sulfinyl Group
Author(s) -
Ruano José Luis García,
Marcos Vanesa,
Alemán José
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900448
Subject(s) - stereoselectivity , regioselectivity , chemistry , group (periodic table) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
No hurdle is too high : The regioselectivity and stereoselectivity of the halohydroxylation of non‐activated allenes are controlled by a remote sulfinyl group through anchimeric assistance (see scheme). The resulting halohydrines are excellent chiral targets for the preparation of optically pure propargylic alcohols and Baylis–Hillman‐type products.