One-carbon homologation of unsymmetrical ketones through magnesium β-oxido carbenoid rearrangement and trapping the enolate intermediates with electrophiles

S Tanaka, T Anai, M Tadokoro, T Satoh

Index: Tanaka, Shu; Anai, Takehiro; Tadokoro, Makoto; Satoh, Tsuyoshi Tetrahedron, 2008 , vol. 64, # 30-31 p. 7199 - 7210

Full Text: HTML

Citation Number: 10

Abstract

A procedure for one-carbon homologation of unsymmetrical ketones, including one-carbon ring-expansion of 2-substituted cyclohexanones, through magnesium β-oxido carbenoid rearrangement as the key reaction is described. Addition of the α-sulfinyl carbanion of 1- chloroethyl p-tolyl sulfoxide to an unsymmetrical ketone gave two diastereomers as adducts in good yields. The adducts were treated with a base to give alkoxides, which were treated ...