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Enantioselective Synthesis of Siloxyallenes from Alkynoylsilanes by Reduction and a Brook Rearrangement and Their Subsequent Trapping in a [4+2] Cycloaddition
Author(s) -
Sasaki Michiko,
Kondo Yasuhiro,
Kawahata Masatoshi,
Yamaguchi Kentaro,
Takeda Kei
Publication year - 2011
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/anie.201102430
Subject(s) - enantioselective synthesis , electrophile , cycloaddition , chemistry , selectivity , lithium (medication) , combinatorial chemistry , amide , reduction (mathematics) , stereochemistry , organic chemistry , catalysis , psychology , geometry , mathematics , psychiatry
Two flavors of selectivity : An enantioselective Meerwein–Ponndorf–Verley‐type reduction of alkynoylsilanes by a chiral lithium amide followed by a Brook rearrangement and S E 2′ electrophilic substitution provides the title compounds in a one‐pot process. In the case of enynoylsilanes, the generated vinylallenes undergo in situ [4+2] cycloaddition to afford highly functionalized polycyclic compounds with unusual facial selectivity.