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Hydrostannylation–Cross‐Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β‐Unsaturated Esters
Author(s) -
Fujiwara Shinichi,
Cadou Romain,
Yamaoka Yousuke,
Takasu Kiyosei,
Yamada Kenichi
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.201403429
Subject(s) - stille reaction , chemistry , stereoselectivity , coupling (piping) , coupling reaction , catalysis , combinatorial chemistry , organic chemistry , engineering , mechanical engineering
A method for the stereoselective synthesis of alkylidenemalonates and related α,β‐unsaturated esters by a hydrostannylation–cross‐coupling process has been developed. Pd‐catalyzed and radical hydrostannylation of propiolate derivatives stereoselectively provided α‐alkoxycarbonyl ( E )‐ and ( Z )‐vinylstannanes, respectively, which were then converted into alkylidenemalonates by the Stille coupling reaction. A one‐pot process was also realizable for the Pd‐catalyzed reactions.