Asymmetric dihydroxylation of heteroaromatic acrylates

被引：15

作者：

Feng, ZX ^{[1
]}

Zhou, WS ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 03期

基金：

中国国家自然科学基金;

关键词：

asymmetric dihydroxylation; heteroaromatic acrylates; building blocks;

D O I：

10.1016/S0040-4039(02)02605-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N- and O-Heteroaromatic acrylates were dihydroxylated with high ee's and good yields. While the AD of pyridyl and pyrryl acrylates afforded diverse yields under the present reaction condition, some corresponding N-substituted pyridyl and pyrryl acrylates (1d, 1e, 1g) proved to be appropriate substrates. The diols obtained can be used as chiral building blocks for the synthesis of various biologically active molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：493 / 495

页数：3

共 37 条

[1]

AHMED EN, 2000, TETRAHEDRON, P8579

[2] 1′-azido- and 1′-amino-1,3-dioxolan-4-ones [J].

Battaglia, A ;

Barbaro, G ;

Giorgianni, P ;

Guerrini, A ;

Pepe, A .

TETRAHEDRON-ASYMMETRY, 2001, 12 (07) :1015-1023

[3] First controlled asymmetric dihydroxylation of thiophene acrylates [J].

Bonini, C ;

D'Auria, M ;

Fedeli, P .

TETRAHEDRON LETTERS, 2002, 43 (21) :3813-3815

[4] Total synthesis of (-)- and (+)-lentiginosine [J].

Chandra, KL ;

Chandrasekhar, M ;

Singh, VK .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4630-4633

[5]

CHEN WP, 1999, J CHEM SOC P1, V2, P103

[6]

D'Auria M, 2000, EUR J ORG CHEM, V2000, P3265

[7] A novel concise total synthesis of (+)-lentiginosine [J].

Feng, ZX ;

Zhou, WS .

TETRAHEDRON LETTERS, 2003, 44 (03) :497-498

[8] Enantioselective synthesis of 5-substituted α,β-unsaturated δ-lactones:: application to the synthesis of styryllactones [J].

Harris, JM ;

O'Doherty, GA .

TETRAHEDRON LETTERS, 2000, 41 (02) :183-187

[9] Directed and undirected asymmetric dihydroxylation reactions:: application in the synthesis of a C-linked analogue of allolactose [J].

Hodgson, R ;

Mahid, T ;

Nelson, A .

CHEMICAL COMMUNICATIONS, 2001, (20) :2076-2077

[10] Aryl-Pd covalently bonded palladacycles, novel amino and oxime catalysts {di-μ-chlorobis(benzaldehydeoxime-6-C,N)dipalladium(II), di-μ-chlorobis(dimethylbenzylamine-6-C,N)dipalladium(II)} for the Heck reaction [J].

Iyer, S ;

Ramesh, C .

TETRAHEDRON LETTERS, 2000, 41 (46) :8981-8984

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