DIASTEREOSELECTIVE CATALYTIC ASYMMETRIC NITROALDOL REACTION UTILIZING RARE EARTH-LI-(R)-BINOL COMPLEX - A HIGHLY EFFICIENT SYNTHESIS OF NORSTATINE

被引：111

作者：

SASAI, H

KIM, WS

SUZUKI, T

SHIBASAKI, M

MITSUDA, M

HASEGAWA, J

OHASHI, T

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

[2] KANEKA CORP,BIOCHEM RES LABS,TAKASAGO,HYOGO 676,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 33期

关键词：

D O I：

10.1016/0040-4039(94)88093-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rare earth-Li-BINOL complexes were used to catalyze nitroaldol reactions of optically active alpha-amino-aldehydes with nitromethane in a highly diastereoselective manner. A typical adduct, (2S, 3S)-3-phthaloylamino-2-hydroxy-1-nitro-4- phenylbutane was conveniently converted to (2S, 3S)-3-amino-2- hydroxy-4-phenylbutanoic acid (erythro-AHPA; phenylnorstatine), a component of the HIV protease inhibitor KNI-227 and KNI-272.

引用

收藏

页码：6123 / 6126

页数：4

相关论文

共 19 条

[1]

FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676

[2] N-QUATERNARY COMPOUNDS .39. CIRCULAR-DICHROISM OF ALPHA-TRIMETHYLAMMONIO ALDEHYDES [J].

GACEK, M ;

UNDHEIM, K .

TETRAHEDRON, 1974, 30 (23-2) :4233-4237

[3] STEREOSELECTION IN THE SYNTHESIS OF THREO-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC AND ERYTHRO-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID USING CHIRAL ACETAL TEMPLATES [J].

HERRANZ, R ;

CASTROPICHEL, J ;

VINUESA, S ;

GARCIALOPEZ, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :938-939

[4]

HERRANZ R, 1989, SYNTHESIS-STUTTGART, P703

[5]

ITO A, 1975, CHEM PHARM BULL, V23, P3081

[6] OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS [J].

JURCZAK, J ;

GOLEBIOWSKI, A .

CHEMICAL REVIEWS, 1989, 89 (01) :149-164

[7] INVITRO ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) ACTIVITIES OF TRANSITION-STATE MIMETIC HIV PROTEASE INHIBITORS CONTAINING ALLOPHENYLNORSTATINE [J].

KAGEYAMA, S ;

MIMOTO, T ;

MURAKAWA, Y ;

NOMIZU, M ;

FORD, H ;

SHIRASAKA, T ;

GULNIK, S ;

ERICKSON, J ;

TAKADA, K ;

HAYASHI, H ;

BRODER, S ;

KISO, Y ;

MITSUYA, H .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1993, 37 (04) :810-817

[8] AN ENANTIODIVERGENT SYNTHESIS OF THREO BETA-AMINO ALCOHOLS - PREPARATION OF KEY INTERMEDIATES FOR BESTATIN AND THE RELATED PEPTIDES [J].

KAWABATA, T ;

KIRYU, Y ;

SUGIURA, Y ;

FUJI, K .

TETRAHEDRON LETTERS, 1993, 34 (32) :5127-5130

[9] A STEREOSELECTIVE SYNTHESIS OF THE (2R,3S)-3-AMINO-2-HYDROXYBUTYRIC AND (2S,3R)-3-AMINO-2-HYDROXYBUTYRIC ACID-DERIVATIVES, THE KEY COMPONENTS OF A RENIN INHIBITOR AND BESTATIN [J].

KOBAYASHI, Y ;

TAKEMOTO, Y ;

KAMIJO, T ;

HARADA, H ;

ITO, Y ;

TERASHIMA, S .

TETRAHEDRON, 1992, 48 (10) :1853-1868

[10]

MIMOTO T, 1992, CHEM PHARM BULL, V40, P2251