AZINOTHRICIN SYNTHETIC STUDIES .1. EFFICIENT ASYMMETRIC SYNTHESES OF (3R)-PIPERAZIC AND (3S)-PIPERAZIC ACIDS

被引：43

作者：

HALE, KJ

DELISSER, VM

MANAVIAZAR, S

机构：

[1] The Christopher Ingold Laboratories, Department of Chemistry, University College London, London, WC1H OAJ England

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)60838-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient asymmetric synthesis of both (3R)- and (3S)-piperazic acids has been developed that is based on electrophilic hydrazination of a chiral bromovaleryl carboximide enolate with di-tert-butyl azodicarboxylate, followed by subsequent intramolecular S(N)2 displacement of the bromide by the resulting substituted aza anion. The diastereoselectivity of the process is typically greater than 96%.

引用

页码：7613 / 7616

页数：4

共 16 条

[1] AMINO-ACIDS AND PEPTIDES .16. CHARACTERISATION OF MONAMYCINS, MEMBERS OF A NEW FAMILY OF CYCLODEPSIPEPTIDE ANTIBIOTICS
BEVAN, K
DAVIES, JS
HASSALL, CH
MORTON, RB
PHILLIPS, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03): : 514 - &
[2] SYNTHESIS OF THE LIPOPHILIC SIDE-CHAIN OF THE CYCLIC HEXADEPSIPEPTIDE ANTIBIOTIC L-156,602
CALDWELL, CG
RUPPRECHT, KM
BONDY, SS
DAVIS, AA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) : 2355 - 2361
[3] CALDWELL CG, 1990, TETRAHEDRON LETT, V31, P4711
[4] TOTAL SYNTHESIS OF L-156,602, A NOVEL CYCLIC HEXADEPSIPEPTIDE ANTIBIOTIC
DURETTE, PL
BAKER, F
BARKER, PL
BOGER, J
BONDY, SS
HAMMOND, ML
LANZA, TJ
PESSOLANO, AA
CALDWELL, CG
[J]. TETRAHEDRON LETTERS, 1990, 31 (09) : 1237 - 1240
[5] DURETTE PL, 1989, 198TH ACS NAT M MIAM
[6] STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES
EVANS, DA
BRITTON, TC
DOROW, RL
DELLARIA, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) : 6395 - 6397
[7] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS
EVANS, DA
BRITTON, TC
DOROW, RL
DELLARIA, JF
[J]. TETRAHEDRON, 1988, 44 (17) : 5525 - 5540
[8] AMINO-ACIDS AND PEPTIDES .21. SYNTHESIS OF A CONGENER OF THE CYCLOHEXADEPSIPEPTIDE ANTIBIOTIC, MONAMYCIN
HASSALL, CH
JOHNSON, WH
THEOBALD, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1451 - 1454
[9] A NEW DEPSIPEPTIDE ANTIBIOTIC, CITROPEPTIN
HAYAKAWA, Y
NAKAGAWA, M
TODA, Y
SETO, H
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (04): : 1007 - 1011
[10] L-156,602, A C5A ANTAGONIST WITH A NOVEL CYCLIC HEXADEPSIPEPTIDE STRUCTURE FROM STREPTOMYCES-SP MA6348 - FERMENTATION, ISOLATION AND STRUCTURE DETERMINATION
HENSENS, OD
BORRIS, RP
KOUPAL, LR
CALDWELL, CG
CURRIE, SA
HAIDRI, AA
HOMNICK, CF
HONEYCUTT, SS
LINDENMAYER, SM
SCHWARTZ, CD
WEISSBERGER, BA
WOODRUFF, HB
ZINK, DL
ZITANO, L
FIELDHOUSE, JM
ROLLINS, T
SPRINGER, MS
SPRINGER, JP
[J]. JOURNAL OF ANTIBIOTICS, 1991, 44 (02) : 249 - 254

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