159763-13-0Relevant articles and documents
New Method for Generation of β-Oxido Carbenoid via Ligand Exchange Reaction of Sulfoxides: A Versatile Procedure for One-Carbon Homologation of Carbonyl Compounds
Satoh, Tsuyoshi,Itoh, Norifumi,Gengyo, Kaoru,Takada, Sae,Asakawa, Naoyuki,et al.
, p. 11839 - 11852 (2007/10/02)
A new procedure for one-carbon homologation of carbonyl compounds is described.The method is based on the rearrangement of β-oxido carbenoid which is generated via the ligand exchange reaction of the sulfinyl group of α-chloro β-hydroxy sulfoxide with tert-butyllithium.Addition of the carbanion of aryl 1-chloroalkyl sulfoxides to carbonyl compounds gave the adducts in good yields.The β-oxido carbenoid rearrangement of the adducts gave one-carbon homologated carbonyl compounds having an α-alkyl substituent.A similar reaction of the adducts derived from carbonyl compounds with chloromethyl p-tolyl sulfoxide yielded a procedure for a methylene insertion.The stereochemistry of the β-oxido carbenoid rearrangenment is also discussed.
1-Chloroalkyl p-Tolyl Sulfoxides as Acetylide Anion Equivalent: A Novel Synthesis Including Asymmetric Synthesis of Propargylic Alcohols from Carbonyl Compounds
Satoh, Tsuyoshi,Hayashi, Yasumasa,Yamakawa, Koji
, p. 2153 - 2158 (2007/10/02)
Addition of the carbanion of 1-chloroalkyl p-tolyl sulfoxide to carbonyl compounds gave the adducts, which were heated in refluxing toluene or xylene to give vinyl chlorides in high overall yield.Dehydrochlorination of the vinyl chlorides with excess n-BuLi afforded propargylic alcohols in high yields.Asymmetric synthesis of both enantiomers of the propargylic alcohols was realized using optically active 1-chloroalkyl p-tolyl sulfoxide and aldehyde.
