31350-94-4Relevant academic research and scientific papers
A Novel Approach to the Asymmetric Synthesis of Epoxides, Allylic Alcohols, α-Amino Ketones, and α-Amino Aldehydes from Carbonyl Compounds through α,β-Epoxy Sulfoxides Using the Optically Active p-Tolylsulfinyl Group To Induce Chirality
Satoh, Tsuyoshi,Oohara, Teruhiko,Ueda, Yoshiko,Yamakawa, Koji
, p. 3130 - 3136 (2007/10/02)
A practical and relatively inexpensive procedure for the preparation of (-)-chloromethyl p-tolyl sulfoxide of high optical purity was accomplished by the chlorination of optically pure (+)-methyl p-tolyl sulfoxide with N-chlorosuccinimide in the presence of K2CO3.The (-)-chloromethyl p-tolyl sulfoxide was alkylated to give a diastereomeric mixture of (-)-1-chloroalkyl p-tolyl sulfoxides.Addition of the anion derived from these sulfoxides to ketones or aldehydes afforded chlorohydrins in quite good yields with complete 1,2-asymmetric induction.Treatment of these chlorohydrins with a base gave optically active α,β-epoxy sulfoxides.On treatment with n-BuLi, the α,β-epoxy sulfoxides gave epoxides or allylic alcohols of high optical purity.This novel procedure was applied to a short synthesis of optically active (+)-disparlure, the sex attractant of the female gypsy moth.Aminolysis of the α,β-epoxy sulfoxides gave optically active α-amino ketones and α-amino aldehydes in quite good yields.
THE PRACTICAL PROCEDURE FOR A PREPARATION OF 1-CHLOROALKYL p-TOLYL SULFOXIDES IN HIGH OPTICALLY ACTIVE FORM: A VERY SHORT SYNTHESIS OF OPTICALLY ACTIVE DISPARLURE
Satoh, Tsuyoshi,Oohara, Teruhiko,Ueda, Yoshiko,Yamakawa, Koji
, p. 313 - 316 (2007/10/02)
A chlorination of optically active alkyl p-tolyl sulfoxides with N-chlorosuccinimide in dichloromethane in the presence of potassium carbonate afforded optically active 1-chloroalkyl p-tolyl sulfoxides in 87-94percent ee (88-94percent chemical yields).The optically active chloroalkyl sulfoxide was applied to a synthesis of optically active (+)-disparlure.
Solid-Phase Silica-Gel Catalyzed α-Halogenation of Alkyl Aryl Sulfoxides with N-Halosuccinimides
Drabowicz, Jozef
, p. 831 - 833 (2007/10/02)
Alkyl aryl sulfoxides are readily halogenated by silica-gel supported N-halosuccinimides.The conversion of optically active alkyl 4-methylphenyl sulfoxides into 1-haloalkyl 4-methylphenyl sulfoxides is accompanied by inversion of configuration at the S-atom.The stereoselectivity of the solid-phase halogenation of alkyl aryl sulfoxides is much higher than that observrd for the halogenation in solution.
