Studies into diastereoselective Dotz benzannulations for the synthesis of axially chiral biaryls

被引：11

作者：

Anderson, JC ^{[1
]}

Cran, JW

King, NP

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 42期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2003.08.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of racemic chiral ortho substituents on 1-phenythex-1-yne have been found to control the atroposelective formation of a biaryl from Dotz benzannulation with pentacarbonyl(methoxyphenylmethylene)chromium(0). The results show there is a subtle balance between the chiral ortho substituent controlling atroposelectivity with a dr 3-5:1 and allowing benzannulation to proceed in yields of 44-67%. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7771 / 7774

页数：4

共 38 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].

ALEXAKIS, A ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511

[2] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].

AMATORE, C ;

BLART, E ;

GENET, JP ;

JUTAND, A ;

LEMAIREAUDOIRE, S ;

SAVIGNAC, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839

[3] Steric and electronic limitations for the Dotz benzannulation of aromatic alkynes [J].

Anderson, JC ;

Cran, JW ;

King, NP .

TETRAHEDRON LETTERS, 2002, 43 (21) :3849-3852

[4] Investigations into ambient temperature biaryl coupling reactions [J].

Anderson, JC ;

Namli, H ;

Roberts, CA .

TETRAHEDRON, 1997, 53 (44) :15123-15134

[5] Reaction of Fischer carbene complexes with 1,3-butadiynes: A new strategem for biaryl synthesis with construction of the biaryl bond preceding synthesis of the arenes [J].

Bao, JM ;

Wulff, WD ;

Fumo, MJ ;

Grant, EB ;

Heller, DP ;

Whitcomb, MC ;

Yeung, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) :2166-2181

[6] Stereoselective total synthesis of axially chiral natural products via biaryl lactones [J].

Bringmann, G ;

Menche, D .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) :615-624

[7] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents [J].

Bringmann, G ;

Breuning, M ;

Tasler, S .

SYNTHESIS-STUTTGART, 1999, (04) :525-558

[8] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[9] The first asymmetric Suzuki cross-coupling reaction [J].

Cammidge, AN ;

Crépy, KVL .

CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724

[10] Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium-chiral phosphine ratio [J].

Castanet, AS ;

Colobert, F ;

Broutin, PE ;

Obringer, M .

TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :659-665

← 1 2 3 4 →