The first example of enamine -: Lewis acid cooperative bifunctional catalysis:: application to the asymmetric aldol reaction

被引：41

作者：

Arnold, Kenny ^{[1
]}

Batsanov, Andrei S. ^{[1
]}

Davies, Bryan ^{[2
]}

Grosjean, Christophe ^{[1
]}

Schuetz, Thorben ^{[1
]}

Whiting, Andrew ^{[1
]}

Zawatzky, Kerstin ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 33期

关键词：

D O I：

10.1039/b806779a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-Sparteine directed lithiation of N-Boc-pyrrolidine, alkylation with chloromethylboronate pinacol ester and acid-based deprotection provides homoboroproline HX salt in 94% ee, which is then an efficient enamine-type pyrrolidine catalyst in an asymmetric aldol reaction when neutralised and especially when esterified in situ with a tartrate ester, for example, providing 90% ee of the aldol adduct derived from acetone and p-nitrobenzaldehyde.

引用

页码：3879 / 3881

页数：3

共 43 条

[1] A catalytic aldol reaction and condensation through in situ boron "Ate" complex enolate generation in water [J].

Aelvoet, Karel ;

Batsanov, Andrei S. ;

Blatch, Alexandrea J. ;

Grosjean, Christophe ;

Patrick, Leonard G. F. ;

Smethurst, Christian A. ;

Whiting, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :768-770

[2] Asymmetric direct amide synthesis by kinetic amine resolution:: A chiral bifunctional aminoboronic acid catalyzed reaction between a racemic amine and an achiral carboxylic acid [J].

Arnold, Kenny ;

Davies, Bryan ;

Herault, Damien ;

Whiting, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2673-2676

[3] Synthesis, evaluation and application of novel bifunctional N,N-di-isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines [J].

Arnold, Kenny ;

Batsanov, Andrei S. ;

Davies, Bryan ;

Whiting, Andrew .

GREEN CHEMISTRY, 2008, 10 (01) :124-134

[4] To catalyze or not to catalyze? Insight into direct amide bond formation from amines and carboxylic acids under thermal and catalyzed conditions [J].

Arnold, Kenny ;

Davies, Bryan ;

Giles, Richard L. ;

Grosjean, Christophe ;

Smith, Gillian E. ;

Whiting, Andrew .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :813-820

[5] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[6] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[7] A (-)-sparteine-directed highly enantioselective synthesis of boroproline.: Solid- and solution-state structure and properties [J].

Batsanov, Andrei S. ;

Grosjean, Christophe ;

Schuetz, Thorben ;

Whiting, Andrew .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6276-6279

[8] Synthesis and structure of planar chiral, bifunctional aminoboronic acid ferrocene derivatives [J].

Batsanov, Andrei S. ;

Herault, Damien ;

Howard, Judith A. K. ;

Patrick, Leonard G. F. ;

Probert, Michael R. ;

Whiting, Andrew .

ORGANOMETALLICS, 2007, 26 (09) :2414-2419

[9] COMPLEX-INDUCED PROXIMITY EFFECTS - ENANTIOSELECTIVE SYNTHESES BASED ON ASYMMETRIC DEPROTONATIONS OF N-BOC-PYRROLIDINES [J].

BEAK, P ;

KERRICK, ST ;

WU, SD ;

CHU, JX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3231-3239

[10]

Bertini Gross K. M., 2001, J AM CHEM SOC, V123, P315

← 1 2 3 4 5 →