The Journal of Organic Chemistry

Threo-N, N'-Bis (. alpha.-methylbenzyl) sulfamide: a readily available chiral ligand for asymmetric lithium aluminum hydride reductions

JM Hawkins, KB Sharpless

Index: Hawkins, Joel M.; Sharpless, K. Barry Journal of Organic Chemistry, 1984 , vol. 49, # 20 p. 3861 - 3862

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Citation Number: 17

Abstract

4 LiAlH, + 4 + 4 HNMeBn - RAR' R AR' (2) THF, -2OOC Conditions were optimized by using n-butyl 2-naphthyl ketone (2) as a substrate due to ready measurement of the resulting enantiomeric excess by chiral stationary-phase ... (1) Presented at the 187th National Meeting of the American Chem- ical Society, St. Louis, MO, April 12,1984. A preliminary account of this work was presented at the 28th National Organic Chemistry Symposium, Bozeman, MT, June 23, 1983. (2) ...