ISSN:
0899-0042
Keywords:
cyclic formyl-monoterpenes
;
tricyclic formyl-sesquiterpenes
;
homogeneous catalyst
;
rhodium-phosphine catalyst
;
platinum-phosphine-tin(II)chloride catalyst
;
hydroformylation
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The hydroformylation of (+)-(R)-limonene (1), (+)-(1R)-isolimonene (2), camphene (3), and (+)-β-cedrene (4) resulted in the regiospecific formation of the corresponding linear aldehyde in the presence of homogeneous platinum and, in some cases, rhodium catalysts. The epimeric composition could be influenced slightly by optically active catalysts formed with chiral bidentate phosphines. The relative configurations of newly formed stereogenic centers were analyzed by 1H and 13C NMR. The primarily formed aldehydes of (+)-8(15)-cedren-9-ol (5) and γ-gurjunene (6) underwent cyclization, giving a mixture of epimers of tetracyclic terpenes. Despite the moderate diastereoselection, the products are of practical importance due to their highly regioselective formation. © 1995 Wiley-Liss, Inc.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530070303
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