A novel 1,3-central-to-axial chirality induction approach to cyclooctadiene lignans

被引：26

作者：

Baudoin, O ^{[1
]}

Décor, A ^{[1
]}

Cesario, M ^{[1
]}

Guéritte, F ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91128 Palaiseau, France

来源：

SYNLETT | 2003年 / 13期

关键词：

axial chirality; Suzuki coupling; chirality induction; cyclooctadiene lignans;

D O I：

10.1055/s-2003-42039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric synthesis of an axially chiral biaryl, potentially useful intermediate in the synthesis of dibenzocyclooctadiene lignans, has been performed. The key step consisted of a diastereoselective Suzuki coupling between a chiral benzylic alcohol and a sterically hindered boronic ester. The 1,3-induction from the benzylic stereocenter to the biaryl axis proceeded with very good diastereoselectivity.

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收藏

页码：2009 / 2012

页数：4

相关论文

共 29 条

[1]

Ayres D., 1990, CHEM PHARM NATURAL P

[2] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271

[3] Synthesis and biological evaluation of A-ring biaryl-carbamate analogues of rhazinilam [J].

Baudoin, O ;

Claveau, F ;

Thoret, S ;

Herrbach, A ;

Guénard, D ;

Guéritte, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3395-3400

[4] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].

Baudoin, O ;

Cesario, M ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207

[5]

BRINGMANN G, 2001, PROGR CHEM NATURAL P, V82

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

Cammidge, AN ;

Crépy, KVL .

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

[7] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[8] Synthesis and structure of new oxapalladacycles with a Pd-O bond [J].

Fernández-Rivas, C ;

Cárdenas, DJ ;

Martín-Matute, B ;

Monge, A ;

Gutiérrez-Puebla, E ;

Echavarren, AM .

ORGANOMETALLICS, 2001, 20 (14) :2998-3006

[9] Kinetic resolution of racemic secondary alcohols by Ru-II-catalyzed hydrogen transfer [J].

Hashiguchi, S ;

Fujii, A ;

Haack, KJ ;

Matsumura, K ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) :288-290

[10] Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling [J].

Herrbach, A ;

Marinetti, A ;

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4897-4905