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Asymmetric hydroformylation of mono‐ and sesquiterpenes
Author(s) -
Kollár László,
Bóadi Gábor
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070303
Subject(s) - hydroformylation , chemistry , stereocenter , epimer , regioselectivity , denticity , limonene , aldehyde , terpene , rhodium , stereochemistry , catalysis , organic chemistry , medicinal chemistry , enantioselective synthesis , crystal structure , essential oil , chromatography
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 1 H and 13 C 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.