Allylation of ketones with a ferrocene-based planar chiral lewis acid

被引：27

作者：

Boshra, Ramez ^{[1
]}

Doshi, Ami ^{[1
]}

Jaekle, Frieder ^{[1
]}

机构：

[1] Rutgers Univ Newark, Dept Chem, Newark, NJ 07102 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 06期

关键词：

allylation; boron; chirality; ferrocene; organoboranes;

D O I：

10.1002/anie.200704687

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Flat, like your hand: The heteronuclear bidentate Lewis acid 1,2-Fc(BMeCl)-(SnMe2Cl) is readily resolved into its constituent enantiomers through highly stereoselective complexation with N-methylpseudoephedrine. The resulting planar chiral Lewis acids show optical purities greater than 97 % and, upon conversion to the respective allylborane derivatives (see scheme), rapidly add to ketones with enantiomeric excess of up to 80 %. (Chemical Equation Presented). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1134 / 1137

页数：4

共 27 条

[1] Mechanistic studies on the B(C6F5)3 catalyzed allylstannation of aromatic aldehydes with ortho donor substituents [J].

Blackwell, JM ;

Piers, WE ;

McDonald, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1295-1306

[2] Binding cooperativity of two different Lewis acid groups at the edge of ferrocene [J].

Boshra, R ;

Sundararaman, A ;

Zakharov, LN ;

Incarvito, CD ;

Rheingold, AL ;

Jäkle, F .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (09) :2810-2824

[3] VERSATILE ALPHA-PINENE-BASED BORANE REAGENTS FOR ASYMMETRIC SYNTHESES [J].

BROWN, HC ;

RAMACHANDRAN, PV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 500 (1-2) :1-19

[4] A convenient method for the generation of allylic dihaloboranes and diallyl(chloro)borane and their application in the allylboration of alkenes and acetylenes [J].

Bubnov, YN ;

Kuznetsov, NY ;

Pastukhov, FV ;

Kublitsky, VV .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (21) :4633-4639

[5] Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes [J].

Burgos, CH ;

Canales, E ;

Matos, K ;

Soderquist, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8044-8049

[6] B-allyl-10-Ph-9-borabicyclo[3.3.2]decanes:: Strategically designed for the asymmetric allylboration of ketones [J].

Canales, E ;

Prasad, KG ;

Soderquist, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11572-11573

[7] A concise update on the applications of chiral ferrocenyl phosphines in homogeneous catalysis leading to organic synthesis [J].

Colacot, TJ .

CHEMICAL REVIEWS, 2003, 103 (08) :3101-3118

[8] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

[9] Applications of planar-chiral heterocycles as ligands in asymmetric catalysis [J].

Fu, Gregory C. .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (11) :853-860

[10]

Gabbai F. P., 2003, ANGEW CHEM, V115, P2318

← 1 2 3 →