Indium-mediated diastereoselective allylation reactions:: preparation of α-hydroxy and α-amino acids

被引：31

作者：

Lee, JG

Choi, KI

Pae, AN

Koh, HY

Kang, YH

Cho, YS

机构：

[1] Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea

[2] Hanyang Univ, Coll Sci, Dept Chem, Ansan 425791, Kyunggi Do, South Korea

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 10期

关键词：

D O I：

10.1039/b110505c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hemiacetals of (+)- and (-)-N-glyoxyloylbornane-10,2-sultam and their imines reacted with allyl iodide in the presence of indium in DMF to give the corresponding alpha-hydroxy and alpha-amino camphor sultam derivatives with high diastereoselectivities (86-90% de). This method could be useful for preparation of alpha-hydroxy and alpha-amino acids.

引用

收藏

页码：1314 / 1317

页数：4

相关论文

共 13 条

[1]

Adam W, 1998, EUR J ORG CHEM, V1998, P2013

[2] Quantitative transformation of racemic 2-hydroxy acids into (R)-2-hydroxy acids by enantioselective oxidation with glycolate oxidase and subsequent reduction of 2-keto acids with D-lactate dehydrogenase [J].

Adam, W ;

Lazarus, M ;

Saha-Möller, CR ;

Schreier, P .

TETRAHEDRON-ASYMMETRY, 1998, 9 (02) :351-355

[3] Influence of Lewis acids on the [4+2] cycloaddition of N,N′-fumaroylbis[(2R)-bornane-10,2-sultam] to cyclopentadiene and application to various dienes [J].

Bauer, T ;

Chapuis, C ;

Kucharska, A ;

Rzepecki, P ;

Jurczak, J .

HELVETICA CHIMICA ACTA, 1998, 81 (02) :324-329

[4] Efficient synthesis of N-glyoxyloyl-(2R)-bornane-10,2-sultam [J].

Bauer, T ;

Jezewski, A ;

Chapuis, C ;

Jurczak, J .

TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1385-1390

[5] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[6] ASYMMETRIC OXYGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-HYDROXY CARBOXYLIC-ACID SYNTHONS [J].

EVANS, DA ;

MORRISSEY, MM ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4346-4348

[7] The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam with 1-pentene and 1-hexene [J].

Jezewski, A ;

Chajewska, K ;

Wielogorski, Z ;

Jurczak, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1741-1749

[8] Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids [J].

Katagiri, N ;

Okada, M ;

Kaneko, C .

TETRAHEDRON LETTERS, 1996, 37 (11) :1801-1804

[9] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS THROUGH ALPHA-IODINATION OF CHIRAL UNSATURATED CARBOXAMIDES AND STEREOSELECTIVE IODOLACTONIZATION [J].

KITAGAWA, O ;

HANANO, T ;

KIKUCHI, N ;

TAGUCHI, T .

TETRAHEDRON LETTERS, 1993, 34 (13) :2165-2168

[10] Enantioselective synthesis of unsaturated α-hydroxy acids [J].

Macritchie, JA ;

Silcock, A ;

Willis, CL .

TETRAHEDRON-ASYMMETRY, 1997, 8 (23) :3895-3902