Tetrahedron letters

First synthesis of simple optically active selenoxides

FA Davis, JM Billmers, OD Stringer

Index: Davis, Franklin A.; Billmers, Joanne M.; Stringer, Orum D. Tetrahedron Letters, 1983 , vol. 24, # 31 p. 3191 - 3194

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Citation Number: 52

Abstract

) was prepared in 96% yield by oxidation of the corresponding selenide using 2-benzenesulfonyl-3-(p-nitrophenyl)oxaziridine 8 and had the following properties: mp 136-8°C (from n-pentane); NMR (CDCl 3 ) δ 1.0-1.5 (m, 18Hm, i-Pr), 2.7-3.1 (m & s, 4H), 3.8-4.2 (quintet, 2H) and 7.2 (s, 2H). The methyl selenide was prepared (86% yield) from 2,4,6-triisopropylphenyl diselenide 10 using NaBH 4 /MeI. Satisfactory elemental ...