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A Convenient and Versatile Method for the Preparation of α‐Hydroxymethyl Ketone Derivatives from the Corresponding Allyl Silyl Ethers or Allyl Carboxylates
Author(s) -
Hon YungSon,
Wong YingChieh,
Wu KuoJui
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800134
Subject(s) - chemistry , silylation , ozonolysis , hydroxymethyl , ketone , organic chemistry , silyl ether , catalysis
The ozonolysis of 1‐substituted allyl silyl ethers or 1‐substituted allyl carboxylates followed by treatment with bases gave the corresponding α‐silyloxymethyl‐ or α‐acyloxymethyl‐ketones in good yields. It is proposed to proceed via the corresponding α‐silyloxy‐ or α‐acyloxyaldehydes intermediates followed by 1,4‐group migration. The results of theoretical calculations are applicable to explain the experimental results.