Hydroboration of Terpenes. IV. Hydroboration of (+)-3-Carene ([UNK] 3-Carene). Configuration Assignments for the 4-Caranols and 4-Caranones. An Unusual …

HC Brown, A Suzuki

Index: Brown,H.C.; Suzuki,A. Journal of the American Chemical Society, 1967 , vol. 89, # 8 p. 1933 - 1941

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Citation Number: 55

Abstract

Abstract:(+)-3-Carene (1) on hydroboration-protonolysis yields cis-carane. Consequently, hydroboration of (+)-3-carene occurs from the side away from the gem-dimethyl group and the hydroboration-oxidation product must be (-)-4-isocaranol (2) and not 4-neocaranol (6) as reported in the literature. Chromic acid-ether oxidation of (-)-4-isocaranol yields (-)-4- isocaranone (3), reduced by lithium trimethoxyaluminohydride to (+)-4-neoisocaranol (5). ...