Two directional chain synthesis. The enantioselective preparation of syn-skipped polyol chains from meso precursors

SL Schreiber, MT Goulet, G Schulte

Index: Schreiber, Stuart L.; Goulet, Mark T.; Schulte, Gayle Journal of the American Chemical Society, 1987 , vol. 109, # 15 p. 4718 - 4720

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Citation Number: 69

Abstract

16 X= l 17 X= NHNH,(excess mesyl chloride and triethylamine in THF at-50" C for 40 min) and subsequent reaction with powdered zinc iodide in methylene chloride at 23" C for 2 h (72% overall yield). Treatment of iodide 16 with excess hydrazine (97%) in 1: l dimethoxyethane-tert-butyl alcohol for 30 min at 23 OC provided the corresponding hydrazine (17, 100%) which after isolation but without purification was stirred in methylene ...