The Journal of Organic Chemistry

Preparation of (R)-(+)-and (S)-(-)-4-iodo-1, 2-epoxybutane [(R)-and (S)-(2-iodoethyl) oxirane], useful chiral synthons

DL Boger, JS Panek

Index: Boger, Dale L.; Panek, James S. Journal of Organic Chemistry, 1981 , vol. 46, # 6 p. 1208 - 1210

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Citation Number: 21

Abstract

Reagents and conditions: a, LiAlH,, THF, reflux; b, CH, SO, Cl, Et, N, CHbCl,,-20 to-15" C; c, cat. CH, SO, H, EtOH, 50 C; d, K, CO,, MeOH-THF, 25" C; e, NaI, acetone, 25" C; f, Ac, O, pyridine, THF, cat. DMAP, 25" C; g, 5% aqueous HCl wash. both (R)-and (59-1 from readily available (S)-(-)-malic acid (2a, natural form), Scheme I. 2 Lithium aluminum hydride reduction of the THP-protected dimethyl ester of (8)-(-)-malic acid [(S)-2c] to give (S)-3alC ...