733016-26-7Relevant articles and documents
A new synthesis of 2-sulfanyl allylic alcohols and α-sulfanyl ketones from carbonyl compounds and 1-chloroalkyl p-tolyl sulfoxides with carbon-carbon bond-formation
Satoh, Tsuyoshi,Takahashi, Yoshinori,Shirai, Yuuichi,Yamada, Yukie
, p. 1734 - 1738 (2007/10/03)
Reaction of lithium α-sulfinyl carbanions of 1-chloroalkyl p-tolyl sulfoxides with ketones or aldehydes at low temperature gave adducts in almost quantitative yields. Treatment of the adducts derived from ketones with trifluoroacetic anhydride (TFAA) in t
A new synthesis of α,α-disubstituted carbonyl compounds from carbonyl compounds with one-carbon homologation
Satoh, Tsuyoshi,Miyashita, Kohsuke
, p. 4859 - 4864 (2007/10/03)
Lithium α-sulfinyl carbanions of 1-chloroalkyl p-tolyl sulfoxides were reacted with carbonyl compounds to afford adducts in high to quantitative yields. The adducts were treated with t-BuMgCl or LDA to give magnesium or lithium alkoxides, which were treated with i-PrMgCl or t-BuLi to afford the enolate with one-carbon elongation through β-oxido carbenoids. The enolate intermediates were found to be able to be trapped with electrophiles to give α,α-disubstituted carbonyl compounds in moderate to good yields. As a whole, this procedure offers a new and good method for synthesis of α,α-disubstituted carbonyl compounds from carbonyl compounds with one-carbon homologation in only two synthetic steps.
