Enantioselective Synthesis of Siloxyallenes from Alkynoylsilanes by Reduction and a Brook Rearrangement and Their Subsequent Trapping in a [4+2] Cycloaddition | Zendy

Sasaki Michiko | Zendy; Kondo Yasuhiro | Zendy; Kawahata Masatoshi | Zendy; Yamaguchi Kentaro | Zendy; Takeda Kei | Zendy

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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.

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