Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate, importance of chirality reversal depending on the palladium-chiral phosphine ratio.

被引：25

作者：

Shimizu, I

Matsumoto, Y

Shoji, K

Ono, T

Satake, A

Yamamoto, A

机构：

[1] Department of Applied Chemistry, School of Science and Engineering, Waseda University, Tokyo 169, Okubo 3-4-1, Shinjuku-ku

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 39期

关键词：

D O I：

10.1016/0040-4039(96)01587-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of (+/-)-8 alpha-methoxycarbonyloxy-4a beta-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (1) in the presence of a palladium-chiral phosphine catalyst gave 4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (2) enantioselectively. When the reaction was carried out using Pd(OAc)(2) and (S)-(-)-BINAP, the enantioselection was influenced by the phosphine to palladium ratio, because (S)-BINAP oxide generated in situ acted as a ligand causing the opposite enantioselectivity. High enantioselectivity (86% ee) was obtained when (1-Me-C3H5-PdCl)(2) and (S)-(-)-p-Tol-BINAP were used. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7115 / 7118

页数：4

共 25 条

[1] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE
AMATORE, C
JUTAND, A
MBARKI, MA
[J]. ORGANOMETALLICS, 1992, 11 (09) : 3009 - 3013
[2] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES
AUBURN, PR
MACKENZIE, PB
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 2033 - 2046
[3] DEHYDRATION STUDIES OF R-4-CHLORO-8A-METHYL-TRANS-DECAHYDRONAPHTHALEN-TERT-4A-OLS AND "CIS-DECAHYDRONAPHTHALEN-TERT-4A-OLS
COXON, JM
GIBSON, JR
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) : 2223 - 2233
[4] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (19) : 3149 - 3150
[5] ALKALI-INDUCED DISPROPORTIONATION OF PALLADIUM(II) TERTIARY PHOSPHINE COMPLEXES, [L2PDCL2], TO LO AND PALLADIUM(0) - KEY INTERMEDIATES IN THE BIPHASIC CARBONYLATION OF ARX CATALYZED BY [L2PDCL2]
GRUSHIN, VV
ALPER, H
[J]. ORGANOMETALLICS, 1993, 12 (05) : 1890 - 1901
[6] CATALYTIC ASYMMETRIC ELIMINATION FORMING CHIRAL 1,3-DIENES VIA PI-ALLYLPALLADIUM INTERMEDIATE
HAYASHI, T
KISHI, K
UOZUMI, Y
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 195 - 198
[7] CATALYTIC ASYMMETRIC ARYLATION OF OLEFINS
HAYASHI, T
KUBO, A
OZAWA, F
[J]. PURE AND APPLIED CHEMISTRY, 1992, 64 (03) : 421 - 427
[8] MODIFICATION OF OPTICALLY-ACTIVE FERROCENYLPHOSPHINE LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION
HAYASHI, T
YAMAMOTO, A
HAGIHARA, T
ITO, Y
[J]. TETRAHEDRON LETTERS, 1986, 27 (02) : 191 - 194
[9] SULFOXIMINE-MEDIATED RESOLUTIONS OF KETONES
JOHNSON, CR
ZELLER, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (14) : 4021 - 4023
[10] ASYMMETRIC-SYNTHESIS - MECHANISM OF ASYMMETRIC CATALYTIC ALLYLATION
MACKENZIE, PB
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 2046 - 2054

← 1 2 3 →