TITANATED METHOXYALLENE AS NOVEL HOMOALDOL EQUIVALENT FOR DIASTEREOSELECTIVE ADDITIONS TO CHIRAL AMINO ALDEHYDES

被引：31

作者：

HORMUTH, S

REISSIG, HU

DORSCH, D

机构：

[1] TECH HSCH DARMSTADT,INST ORGAN CHEM,D-64287 DARMSTADT,GERMANY

[2] PRAKLIN PHARMAFORSCH,D-64271 DARMSTADT,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 10期

关键词：

D O I：

10.1002/anie.199314491

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The versatile building block, methoxyallene reveals another a new facet: The titanium derivative 1 derived from it reacts with aldehydes at the γ position. Thus the methoxyalkynes anti‐3 arise with high anti‐selectivity on reaction of 1 with α‐N,N‐dibenzylamino aldehydes 2. These activated carboxylic acid derivatives can be transformed into the homostatine lactones anti‐4 by hydrolysis. R  CH3, CH2Ph, CH2CHMe2. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1449 / 1450

页数：2

共 28 条

[1] STEREOCONTROLLED ADDITION OF CHIRAL, NONRACEMIC AMIDE HOMOENOLATES TO T-BOC-(S)-PHENYLALANINAL
ARMSTRONG, JD
HARTNER, FW
DECAMP, AE
VOLANTE, RP
SHINKAI, I
[J]. TETRAHEDRON LETTERS, 1992, 33 (44) : 6599 - 6602
[2] BASHA A, 1907, TETRAHEDRON LETT, P4171
[3] BRANDSMA L, 1987, PREPARATIVE POLAR OR, V1, P97
[4] A FACILE ONE-POT SYNTHESIS OF HOMOPROPARGYLIC ALCOHOLS FROM TERMINAL ACETYLENES
BURNS, MR
COWARD, JK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 528 - 532
[5] STEREOCONTROLLED ADDITION OF PROPIONATE HOMOENOLATE EQUIVALENTS TO CHIRAL ALPHA-AMINO ALDEHYDES
DECAMP, AE
KAWAGUCHI, AT
VOLANTE, RP
SHINKAI, I
[J]. TETRAHEDRON LETTERS, 1991, 32 (16) : 1867 - 1870
[6] GELIN R, 1971, B SOC CHIM FR, P4546
[7] AN EFFICIENT SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES - THE CORE UNIT OF POTENT HIV-1 PROTEASE INHIBITORS
GHOSH, AK
MCKEE, SP
THOMPSON, WJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) : 6500 - 6503
[8] RENIN INHIBITORS
GREENLEE, WJ
[J]. MEDICINAL RESEARCH REVIEWS, 1990, 10 (02) : 173 - 236
[9] HAHN G, 1983, SYNTHESIS-STUTTGART, P883
[10] HENNING R, 1990, NACHR CHEM TECH LAB, V38, P460

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