TY - JOUR
T1 - Organoboranes for synthesis 17. Generality of Hydroboration-amination for the conversion of terpenes into enantiomerically pure terpenylamines. The utility for gas chromatographic analysis of chiral carboxylic acids
AU - Brown, Herbert C.
AU - Malhotra, Sanjay V.
AU - Veeraraghavan Ramachandran, P.
PY - 1996/12
Y1 - 1996/12
N2 - The generality of our new convenient synthesis of isopinocampheylamines by hydroboration-amination of α-pinene has been established by converting representative terpenes into optically pure terpenylamines, such as (-)-cis-caran-trans-2-amine, (-)-cis-caran-trans-4-amine, (-)-longifolamine, and (+)-cis-myrtanylamine. The synthesis involves converting the terpene into the B-chloroditerpenylborane by treatment with chloroborane-methyl sulfide. This is treated with trimethylaluminum to form the B-methylditerpenylborane, and the latter is converted into the amine by treatment with hydloxylamine-O-sulfonic acid. cis-Myrtanylamine has been shown to be as effective as isopinocampheylamine for the gas chromatographic analysis of racemic carboxylic acids as their diastereomeric amides, suggesting the generality of this application of terpenylamines as chiral derivatizing agents.
AB - The generality of our new convenient synthesis of isopinocampheylamines by hydroboration-amination of α-pinene has been established by converting representative terpenes into optically pure terpenylamines, such as (-)-cis-caran-trans-2-amine, (-)-cis-caran-trans-4-amine, (-)-longifolamine, and (+)-cis-myrtanylamine. The synthesis involves converting the terpene into the B-chloroditerpenylborane by treatment with chloroborane-methyl sulfide. This is treated with trimethylaluminum to form the B-methylditerpenylborane, and the latter is converted into the amine by treatment with hydloxylamine-O-sulfonic acid. cis-Myrtanylamine has been shown to be as effective as isopinocampheylamine for the gas chromatographic analysis of racemic carboxylic acids as their diastereomeric amides, suggesting the generality of this application of terpenylamines as chiral derivatizing agents.
UR - http://www.scopus.com/inward/record.url?scp=0030561218&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030561218&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(96)00460-0
DO - 10.1016/S0957-4166(96)00460-0
M3 - Article
AN - SCOPUS:0030561218
SN - 0957-4166
VL - 7
SP - 3527
EP - 3534
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 12
ER -