Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives

被引：42

作者：

O'Donnell, MJ ^{[1
]}

Cooper, JT

Mader, MM

机构：

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

[2] Eli Lilly & Co, Lilly Res Labs, Indianapolis, IN 46285 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 09期

关键词：

D O I：

10.1021/ja0298794

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active syn- or anti-β-substituted-α-amino acid derivatives are prepared in 94 to ≥99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride. Copyright © 2003 American Chemical Society.

引用

页码：2370 / 2371

页数：2

共 24 条

[11] Synthesis of (2S,3S)-β-methyltryptophan [J].

Han, GX ;

Lewis, A ;

Hruby, VJ .

TETRAHEDRON LETTERS, 2001, 42 (28) :4601-4603

[12] CATALYTIC ASYMMETRIC HYDROBORATION OF STYRENES [J].

HAYASHI, T ;

MATSUMOTO, Y ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3426-3428

[13] THEORETICAL-STUDIES OF STEREOSELECTIVE HYDROBORATIONS [J].

HOUK, KN ;

RONDAN, NG ;

WU, YD ;

METZ, JT ;

PADDONROW, MN .

TETRAHEDRON, 1984, 40 (12) :2257-2274

[14]

Krause N, 1997, LIEBIGS ANN-RECL, P2409

[15] Progress toward the total synthesis of callipeltin A (I):: Asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine [J].

Liang, B ;

Carroll, PJ ;

Joullié, MM .

ORGANIC LETTERS, 2000, 2 (26) :4157-4160

[16] α-halo boronic esters in asymmetric synthesis [J].

Matteson, DS .

TETRAHEDRON, 1998, 54 (36) :10555-10606

[17]

Medina E, 2000, HELV CHIM ACTA, V83, P972, DOI 10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.3.CO

[18]

2-0

[19] Around and beyond Cram's rule [J].

Mengel, A ;

Reiser, O .

CHEMICAL REVIEWS, 1999, 99 (05) :1191-1223

[20] The enantioselective synthesis of α-amino acid derivatives via organoboranes [J].

O'Donnell, MJ ;

Drew, MD ;

Cooper, JT ;

Delgado, F ;

Zhou, CY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9348-9349

← 1 2 3 →