Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition

被引：86

作者：

Hodgson, DM ^{[1
]}

Stupple, PA ^{[1
]}

Johnstone, C ^{[1
]}

机构：

[1] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(97)01480-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition of alpha-diazo-beta-ketoesters 1 (R = alkyl, n = 1,2) using 1 mol% [Rh-2(S-DOSP)(4)] 2 in hexane at room temperature to give the cycloadducts 3 in good yields and up to 53% ee are described. (C) 1997 Elsevier Science Ltd.

引用

页码：6471 / 6472

页数：2

共 11 条

[1] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS
BROOKS, DW
LU, LDL
MASAMUNE, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01): : 72 - 74
[2] Calter MA, 1997, CURR ORG CHEM, V1, P37
[3] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
Davies, HML
Bruzinski, PR
Lake, DH
Kong, N
Fall, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) : 6897 - 6907
[4] Rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed asymmetric insertions of vinyl- and phenylcarbenoids into the Si-H bond
Davies, HML
Hansen, T
Rutberg, J
Bruzinski, PR
[J]. TETRAHEDRON LETTERS, 1997, 38 (10) : 1741 - 1744
[5] Doyle MP, 1997, CHEM COMMUN, P983
[6] A cycloaddition-rearrangement approach to the squalestatins
Hodgson, DM
Bailey, JM
Harrison, T
[J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4623 - 4626
[7] Cascade processes of metallo carbenoids
Padwa, A
Weingarten, MD
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 223 - 269
[8] REACTIVITY PATTERNS IN THE RHODIUM CARBENOID INDUCED TANDEM CYCLIZATION CYCLO-ADDITION REACTION
PADWA, A
HORNBUCKLE, SF
FRYXELL, GE
STULL, PD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) : 817 - 824
[9] Ligand-induced selectivity in the rhodium(II)-catalyzed reactions of alpha-diazo carbonyl compounds
Padwa, A
Austin, DJ
Hornbuckle, SF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 63 - 72
[10] TANDEM CYCLIZATION CYCLOADDITION REACTION OF RHODIUM CARBENOIDS - STUDIES DEALING WITH INTRAMOLECULAR CYCLOADDITIONS
PADWA, A
HORNBUCKLE, SF
FRYXELL, GE
ZHANG, ZJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) : 5747 - 5757

← 1 2 →