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Paper | Regular issue | Vol 81, No. 5, 2010, pp.1239-1251
Published online, 24th March, 2010
DOI: 10.3987/COM-10-11922
Synthesis of (3S)-2,5-Diethoxy-3,6-dihydro-3-isopropyl-6-methylsulfanylpyrazines and Stereoselectivity in Alkylation of the Anions

Yoshihide Usami,* Masao Arimoto,* Chisaka Kioka, Masako Yamanaka, Naoko Matsuda, and Hayato Ichikawa

*Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan

Abstract

The introduction of a sulfur function into Schöllkopf’s bislactim ether was carried out to synthesize the diastereomers of (3S)-2,5-diethoxy-3,6-dihydro-3-isopropyl-6-methylsulfanylpyrazine. Stereoselectivity in the alkylation of the anions derived from those compounds was examined as a basic study of the synthesis of chiral α-sulfanylamino acids.