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A Convenient Synthesis of α ‐Halomethylene Aldols or β ‐Halo‐ α ‐(hydroxyalkyl)acrylates Using the Chalcogeno‐Baylis–Hillman Reaction
Author(s) -
Kataoka Tadashi,
Kinoshita Hironori,
Kinoshita Sayaka,
Iwamura Tatsunori,
Watanabe Shinichi
Publication year - 2000
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 - 10.1002/1521-3773(20000703)39:13<2358::aid-anie2358>3.0.co;2-y
Subject(s) - selectivity , chemistry , baylis–hillman reaction , halide , halo , sulfide , titanium , organic chemistry , combinatorial chemistry , catalysis , physics , quantum mechanics , galaxy
Alkynes are the substrates in a dimethyl sulfide catalyzed chalcogeno‐Baylis–Hillman reaction involving titanium halides (see scheme). α ‐Halomethylene aldols or β ‐halo‐ α ‐(hydroxyalkyl)acrylates can be prepared readily and diastereoselectively ( E selectivity for the former and Z selectivity for the latter).