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Highly Regio‐ and Stereoselective Iodohydroxylation of 1,2‐Allenylic Sulfoxides in the Presence of Benzyl Thiol
Author(s) -
Wang Minyan,
Fu Chunling,
Ma Shengming
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000973
Subject(s) - chemistry , stereoselectivity , sulfoxide , thiol , sulfur , medicinal chemistry , sulfide , organic chemistry , catalysis
The iodohydroxylation of 1,2‐allenyl sulfoxides with iodine in the presence of benzyl thiol afforded 3‐hydroxy‐2‐iodo‐2( E )‐alkenyl sulfides in good yields and high regio‐ and stereoselectivities. In this reaction it was observed that the sulfoxide functionality was reduced to sulfide and the water in the reaction mixture plays an important role for the stereoselectivity observed. A mechanism involving the attack of benzyl thiol at the positively charged sulfur atom in the five‐membered intermediate 2 has been proposed.