Catalytic enantioselective addition of diorganozinc reagents to vinyl sulfones

被引：44

作者：

Desrosiers, Jean-Nicolas ^{[1
]}

Bechara, William S. ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 11期

关键词：

D O I：

10.1021/ol800747v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the catalytic asymmetric conjugate addition of diorganozinc reagents to vinyl sulfones is reported. Using a Binap circle Cu complex, enantioselectivities up to 98% ee and high yields can be attained for a variety of substrates. Several dialkylzinc reagents are also compatible with this procedure.

引用

页码：2315 / 2318

页数：4

共 40 条

[1]

Bellingham R, 1996, SYNTHESIS-STUTTGART, P285

[2] Modified BINAP: The how and the why [J].

Berthod, M ;

Mignani, G ;

Woodward, G ;

Lemaire, M .

CHEMICAL REVIEWS, 2005, 105 (05) :1801-1836

[3] Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine) monoxide chiral ligand [J].

Boezio, AA ;

Pytkowicz, J ;

Côté, A ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14260-14261

[4] Asymmetric catalytic addition of diorganozinc reagents to imines:: Scope and application [J].

Charette, AB ;

Boezio, AA ;

Côté, A ;

Moreau, E ;

Pytkowicz, J ;

Desrosiers, JN ;

Legault, C .

PURE AND APPLIED CHEMISTRY, 2005, 77 (07) :1259-1267

[5] An expedient approach to E,Z-dienes using the Julia olefination [J].

Charette, AB ;

Berthelette, C ;

St-Martin, D .

TETRAHEDRON LETTERS, 2001, 42 (31) :5149-5153

[6] Catalytic asymmetric addition of diorganozinc reagents to N-phosphinoylalkylimines [J].

Cóté, A ;

Boezio, AA ;

Charette, AB .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5405-5410

[7] General method for the expedient synthesis of salt-free diorganozinc reagents using zinc methoxide [J].

Cote, Alexandre ;

Charette, Andre B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2771-+

[8] Application of the chiral bis(phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to β-nitroalkenes [J].

Cote, Alexandre ;

Lindsay, Vincent N. G. ;

Charette, Andre B. .

ORGANIC LETTERS, 2007, 9 (01) :85-87

[9] Catalytic enantioselective reduction of β,β-disubstituted vinyl phenyl Sulfones by using bisphosphine monoxide Ligands [J].

Desrosiers, Jean-Nicolas ;

Charette, Andre B. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) :5955-5957

[10] PREPARATION OF ENANTIOMERICALLY ENRICHED (1S)-1PHENYLPROPAN-1-AMINE HYDROCHLORIDE BY A CATALYTIC ADDITION OF DIORGANOZINC REAGENTS TO IMINES [Benzenemethanamine,alpha-ethyl-, hydrochloride, (alpha S)-] [J].

Desrosiers, Jean-Nicolas ;

Cote, Alexandre ;

Boezio, Alessandro A. ;

Charette, Andre B. .

ORGANIC SYNTHESES, 2006, 83 :5-+

← 1 2 3 4 →