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1,8‐Bis(allylstannyl)naphthalene Derivatives as Neutral Allylation Agents: Rate Acceleration by Chelation‐Induced Lewis Acidity
Author(s) -
Asao Naoki,
Liu Pingli,
Maruoka Keiji
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199725071
Subject(s) - chemistry , chelation , denticity , naphthalene , stannane , lewis acids and bases , medicinal chemistry , organic chemistry , catalysis , crystal structure
A large variety of carbonyl substrates can be allylated with 1 under neutral conditions. In the case of dicarbonyl compounds, products 2 form chemoselectively. The driving force of this reaction is ascribed to the latent Lewis acidity, which is induced by chelation of neutral, bidentate bis(stannane)s on the carbonyl group (structure A ).
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