O-alkenyl hydroxylamines:: A new concept for cyclofunctionalization

被引：47

作者：

Bates, RW

Sa-Ei, K

机构：

[1] Chulabhorn Res Inst, Med Chem Lab, Bangkok 10210, Thailand

[2] Chulalongkorn Univ, Dept Chem, Bangkok 10330, Thailand

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 24期

关键词：

D O I：

10.1021/ol026701d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of O-homoallylhydroxylamines with palladium(II) and copper(II) in the presence of a base, methanol, and carbon monoxide results in the formation of isooxazolidines. An electron-withdrawing group on the hydroxylamine nitrogen is essential. When carbamate groups are used the products are formed exclusively as their cis isomers.

引用

页码：4225 / 4227

页数：3

共 23 条

[1] Syntheses of the sedum and related alkaloids
Bates, RW
Sa-Ei, K
[J]. TETRAHEDRON, 2002, 58 (30) : 5957 - 5978
[2] Nucleophilic transition metal based cyclization of allenes
Bates, RW
Satcharoen, V
[J]. CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) : 12 - 21
[3] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES
CARDILLO, G
ORENA, M
[J]. TETRAHEDRON, 1990, 46 (10) : 3321 - 3408
[4] COLQUHOUN HM, 1991, CARBONYLATION, P139
[5] COREY EJ, 1978, TETRAHEDRON LETT, P1051
[6] COTTON FA, 1980, ADV INORG CHEM, P801
[7] Electrophile mediated heteroatom cyclizations onto C-C pi-bonds .1. Halogen and chalcogen mediated cyclization
Frederickson, M
Grigg, R
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1997, 29 (01) : 33 - &
[8] Electrophile mediated heteroatom cyclizations onto C-C pi-bonds .2. Metal ion mediated cyclization
Frederickson, M
Grigg, R
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1997, 29 (01) : 63 - 115
[9] GRACZA T, 1992, SYNLETT, P191
[10] CARBAMATE MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .2. REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF 1,3-SYN AND 1,2-ANTI AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION
HIRAMA, M
IWASHITA, M
YAMAZAKI, Y
ITO, S
[J]. TETRAHEDRON LETTERS, 1984, 25 (43) : 4963 - 4964

← 1 2 3 →