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Titanocene( II )‐Promoted Multicomponent Reactions Utilizing Alkynyl Sulfones, Alkenyl Sulfones, and Carbonyl Compounds: A Novel Method for the Synthesis of Vinylallenes
Author(s) -
Ogata Akitoshi,
Nemoto Masami,
Kobayashi Kenji,
Tsubouchi Akira,
Takeda Takeshi
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601326
Subject(s) - stereoselectivity , reagent , chemistry , titanium , medicinal chemistry , sulfone , organic chemistry , catalysis
Titanocene( II )‐promoted cross coupling of alkynyl‐ and ( Z )‐alkenyl sulfones affords α‐(phenylsulfonyl)alkenyltitanium species. Further treatment of these species with the titanocene( II ) reagent generates titanium vinylvinylidene complexes, which react with carbonyl compounds in one pot to produce substituted vinylallenes with complete stereoselectivity. By using α,β‐unsaturated ketones, 1,3,4,6‐tetraenes are also obtained stereoselectively.