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Complete Regio‐ and Stereoselectivity Control in the Halohydroxylation of Non‐activated Allenes Mediated by a Remote Sulfinyl Group
Authors:José Luis García Ruano Prof Dr  Vanesa Marcos  José Alemán Dr
Institution:Departamento de Química Orgánica (C‐I), Universidad Autónoma de Madrid, Cantoblanco, 28049‐Madrid (Spain), Fax: (+34)?91‐497‐466
Abstract: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.
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Keywords:allenes  asymmetric synthesis  halohydroxylation  sulfoxides
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