An efficient homogeneous catalytic enantioselective synthesis of α-amino acid derivatives

被引：153

作者：

O'Donnell, MJ ^{[1
]}

Delgado, F

Hostettler, C

Schwesinger, R

机构：

[1] Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA

[2] Univ Freiburg, Chem Lab, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

关键词：

amino acids and derivatives; alkylation; enantiocontrol; phosphazenes;

D O I：

10.1016/S0040-4039(98)01995-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective alkylation of the benzophenone imine of glycine t-butyl ester is realized by an efficient homogeneous reaction with alkyl halides. the neutral, non-ionic phosphazene base (BEMP or BTPP), and chiral quaternary ammonium salts derived from the cinchona alkaloids. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8775 / 8778

页数：4

共 32 条

[1] ETHYL PHENYLSULFINYL FLUOROACETATE, A NEW AND VERSATILE REAGENT FOR THE PREPARATION OF ALPHA-FLUORO-ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID ESTERS [J].

ALLMENDINGER, T .

TETRAHEDRON, 1991, 47 (27) :4905-4914

[2]

Bezencon O, 1996, LIEBIGS ANN, P1259

[3]

BORDWELL FG, UNPUB

[4] Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].

Corey, EJ ;

Noe, MC ;

Xu, F .

TETRAHEDRON LETTERS, 1998, 39 (30) :5347-5350

[5] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].

Corey, EJ ;

Xu, F ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415

[6] Solid-phase synthesis of substituted glutamic acid derivatives via Michael addition reactions [J].

Domínguez, E ;

O'Donnell, MJ ;

Scott, WL .

TETRAHEDRON LETTERS, 1998, 39 (15) :2167-2170

[7] Synthesis of benzofuran derivatives on solid support via SmI2-mediated radical cyclization [J].

Du, XH ;

Armstrong, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5678-5679

[8]

ESIKOVA IA, 1997, ACS SYM SER, V659, pCH7

[9]

JUN ZD, 1996, TETRAHEDRON LETT, V37, P5249

[10] Synthesis and asymmetric alkylation of glucose-derived bicyclic oxazinones: An evaluation of their use as ''chiral glycines''. [J].

Keynes, MN ;

Earle, MA ;

Sudharshan, M ;

Hultin, PG .

TETRAHEDRON, 1996, 52 (26) :8685-8702

← 1 2 3 4 →