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“Amphiphilic” Cleavage of γ ‐Stannyl Ketones with ATPH/RLi: Application to Enone Fragmentation by the Conjugate Addition – Cleavage Sequence
Author(s) -
Kondo Yuichiro,
Koni Kana,
Iwasaki Atsuko,
Ooi Takashi,
Maruoka Keiji
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/(sici)1521-3773(20000117)39:2<414::aid-anie414>3.0.co;2-9
Subject(s) - enone , conjugate , chemistry , cleavage (geology) , carbanion , nucleophile , michael reaction , bond cleavage , lewis acids and bases , stereochemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , mathematics , geotechnical engineering , fracture (geology) , engineering
The use of a combined Lewis acid/base system consisting of aluminum tris(2,6‐diphenylphenoxide) (ATPH) and MeLi has allowed the electrophilically activated nucleophilic (“amphiphilic”) cleavage of C α −C β bonds in γ ‐stannyl ketones. Through combination with the conjugate addition of α ‐stannyl carbanion to enone, this approach constitutes a novel two‐step conjugate addition – cleavage sequence that leads to functionalized ketones (see reaction).