Synthesis and conformational aspects of cis-and trans-3-carbomethoxy-6-oxabicyclo [3.1. 0] hexane

KE Lizotte, PE Marecki, MP Mertes

Index: Lizotte, Kathryn E.; Marecki, Paul E.; Mertes, Mathias P. Journal of Organic Chemistry, 1983 , vol. 48, # 20 p. 3594 - 3597

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Citation Number: 9

Abstract

(S)-(-)-2, 2, 4-Trimethyl-1, 3-dioxolane-4-carbxaldehyde (1). Procedure A: Swern Oxidation of 2. To a stirred solution of oxalyl chloride (0.24 mL, 2.75 mmol, 1.1 equiv) in CHZCl2 (10 mL) at-78" C was added Me2S0 (0.39 mL, 5.5 mmol, 2.2 equiv) over a 5-min period. After the suspension was stirred for 20 min,(R)-(+)-2 (365 mg, 2.5 mmol, 1.0 equiv) in CH2C12 (3 mL) was added at-78" C. After stirring for 55 min, Et3N (1.75 mL, 12.5 mmol, 5.0 equiv) was ...

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