RHODIUM CATALYZED DECARBONYLATION OF OPTICALLY-ACTIVE CAMPHOLENAL ANALOGS

被引：22

作者：

CHAPUIS, C

WINTER, B

SCHULTELTE, KH

机构：

[1] Firmenich SA, Research Laboratories, CH-1211 Geneva 8

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期

关键词：

DECARBONYLATION; CAMPHOLENAL; WILKINSON AND RHODIUM CATALYST; PULEGONE;

D O I：

10.1016/S0040-4039(00)60025-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Campholenal analogues (+)-1a-d were decarbonylated with a catalytic amount of Rh/Al2O3 with only slight racemization. Experiments with other catalysts showed that racemization increases with the ability of the metal to form a pi-allyl complex and to catalyse the hydrogenation of the beta-elimination side product. (Ph3P)3RhCl gave the best results.

引用

页码：6135 / 6138

页数：4

共 43 条

[1] REACTIONS OF 2-BORNYL RADICAL .2. FREE RADICAL WAGNER-MEERWEIN REARRANGEMENT
BERSON, JA
WALIA, JS
OLSEN, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (17) : 3337 - &
[2] CHEMISTRY OF TERPENES .14. SYNTHESES OF (+/-)- AND (+)-FENCHONE, AND (+)-CIS-2,2,5-TRIMETHYL-3-VINYLCYCLOPENTANONE, A PHOTOISOMER OF (-)-TRANS-CARAN-4-ONE
BOYLE, PH
COCKER, W
GRAYSON, DH
SHANNON, PVR
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (11): : 2136 - &
[3] TOTAL SYNTHESIS OF (+/-)-FENCHONE, A SYNTHESIS OF (+)-FENCHONE AND OF (+)-CIS-2,2,5-TRIMETHYL-3-VINYLCYCLOPENTANONE, A PHOTOISOMER OF (-)-TRANS-CARAN-4-ONE
BOYLE, PH
COCKER, W
GRAYSON, DH
SHANNON, PVR
[J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (08): : 395 - &
[4] CHAPUIS C, 1991, EPA1419860
[5] CHAPUIS C, 1991, EPA1449034
[6] CHAPUIS C, 1990, EPA1374509
[7] CHAPUIS C, 1992, IN PRESS HELV CHIM A, V75
[8] CONIA JM, 1954, MEMOIRES SOC CHIM FR, V1, P943
[9] DESCOTES G, 1968, B SOC CHIM FR, V1, P382
[10] OPTICAL ROTATORY DISPERSION STUDIES .21. EFFECT OF RING SIZE
DJERASSI, C
KRAKOWER, GW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (01) : 237 - 242

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