Liebigs Annalen der Chemie

Stereoselective Syntheses of Alcohols, XXI. Addition of γ??Methoxycrotylboronates to Aldehydes

RW Hoffmann, R Metternich

Index: Hoffmann, Reinhard W.; Metternich, Rainer Liebigs Annalen der Chemie, 1985 , # 12 p. 2390 - 2402

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Citation Number: 8

Abstract

Abstract Starting from 3-methoxy-1, 2-butadiene (12) both E-and Z-γ- methoxycrotylboronates 10 and 11 were prepared in isomeric purities of 85–90%. By addition of the E-isomer 10 to aldehydes the homoallyl alcohols 5 were obtained in high diastereomeric purity. Addition to the lactaldehyde derivatives 21 unexpectedly led to the cyclopropylcarbinols 24 as main products.