STEREOCONTROLLED CONVERGENT SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES BY THE REACTION OF ALPHA-AMINO ALDEHYDE WITH ALKOXYTITANIUM HOMOENOLATES

被引：33

作者：

KANO, S ^{[1
]}

YOKOMATSU, T ^{[1
]}

SHIBUYA, S ^{[1
]}

机构：

[1] TOKYO COLL PHARM,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 02期

关键词：

D O I：

10.1016/0040-4039(91)80863-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (S)-alpha-dibenzylamino aldehydes with dichloroisopropoxy-titanium ester homoenolates gave the corresponding gamma-aminoalkyl gamma-lactones with high erythro selectivity. The same reaction by the use of amide homoenolates also afforded the corresponding 2-amino alcohols with high erythro-selectivity.

引用

页码：233 / 236

页数：4

共 14 条

[1] AGAWAL NS, 1986, J MED CHEM, V29, P2519
[2] AN EFFICIENT SYNTHESIS OF THE GAMMA-LACTONE CORRESPONDING TO A HYDROXYETHYLENE DIPEPTIDE ISOSTERE USING STEREOSELECTIVE BROMOLACTONIZATION OF A CHIRAL ACYLOXAZOLIDINONE
BRADBURY, RH
REVILL, JM
RIVETT, JE
WATERSON, D
[J]. TETRAHEDRON LETTERS, 1989, 30 (29) : 3845 - 3848
[3] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[4] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS
EVANS, DA
BRITTON, TC
ELLMAN, JA
DOROW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4011 - 4030
[5] A SHORT, STEREOSELECTIVE SYNTHESIS OF THE LACTONE PRECURSOR TO 2R,4S,5S HYDROXYETHYLENE DIPEPTIDE ISOSTERES
FRAY, AH
KAYE, RL
KLEINMAN, EF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) : 4828 - 4833
[6] A NEW METHOD FOR GENERATING TRICHLOROTITANIUM(IV) ESTER HOMOENOLATES - DIRECT TIN TITANIUM EXCHANGE
GOSWAMI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) : 5907 - 5909
[7] A STEREOCONTROLLED SYNTHESIS OF (-)-BESTATIN FROM AN ACYCLIC ALLYLAMINE BY IODOCYCLOCARBAMATION
KOBAYASHI, S
ISOBE, T
OHNO, M
[J]. TETRAHEDRON LETTERS, 1984, 25 (44) : 5079 - 5082
[8] TRICHLOROTITANIUM AND ALKOXYTITANIUM HOMOENOLATES - PREPARATION, CHARACTERIZATION, AND UTILIZATION FOR ORGANIC-SYNTHESIS
NAKAMURA, E
OSHINO, H
KUWAJIMA, I
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (13) : 3745 - 3755
[9] OXIDATION OF ALCOHOLS BY ACTIVATED DIMETHYL-SULFOXIDE - PREPARATIVE, STERIC AND MECHANISTIC STUDY
OMURA, K
SWERN, D
[J]. TETRAHEDRON, 1978, 34 (11) : 1651 - 1660
[10] STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS FROM OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS
REETZ, MT
DREWES, MW
SCHMITZ, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1141 - 1143

← 1 2 →