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

页码：6123 / 6126

页数：4

共 19 条

[1] FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676
[2] N-QUATERNARY COMPOUNDS .39. CIRCULAR-DICHROISM OF ALPHA-TRIMETHYLAMMONIO ALDEHYDES
GACEK, M
UNDHEIM, K
[J]. 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
HERRANZ, R
CASTROPICHEL, J
VINUESA, S
GARCIALOPEZ, T
[J]. 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
JURCZAK, J
GOLEBIOWSKI, A
[J]. CHEMICAL REVIEWS, 1989, 89 (01) : 149 - 164
[7] INVITRO ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) ACTIVITIES OF TRANSITION-STATE MIMETIC HIV PROTEASE INHIBITORS CONTAINING ALLOPHENYLNORSTATINE
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
[J]. 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
KAWABATA, T
KIRYU, Y
SUGIURA, Y
FUJI, K
[J]. 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
KOBAYASHI, Y
TAKEMOTO, Y
KAMIJO, T
HARADA, H
ITO, Y
TERASHIMA, S
[J]. TETRAHEDRON, 1992, 48 (10) : 1853 - 1868
[10] MIMOTO T, 1992, CHEM PHARM BULL, V40, P2251

← 1 2 →