Chiral tetraalkylmethanes. Two syntheses of optically active butylethylmethylpropylmethane of known and high optical purity

W Ten Hoeve, H Wynberg

Index: Hoeve, Wolter Ten; Wynberg, Hans Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2754 - 2763

Full Text: HTML

Citation Number: 9

Abstract

The chiral hydrocarbon butylethylmethylpropylmethane (10) has been prepared in a state of known and high optical purity via two independent routes. The first synthesis has as its main feature the addition of 2-thienylmagnesium bromide to the a, p-unsaturated di-(-)-menthyl ester 11. The two diastereoisomeric adducts 12 were readily separated by crystallization, as confirmed by'Hnmr spectroscopy. Saponification gave the thiophene acid 24. Further ...