ASYMMETRIC-SYNTHESIS .32. A NEW ACCESS TO ENANTIOMERICALLY PURE (S)-(-)-PIPECOLIC ACID AND 2-ALKYLATED OR 6-ALKYLATED DERIVATIVES

被引：68

作者：

BERRIEN, JF ^{[1
]}

ROYER, J ^{[1
]}

HUSSON, HP ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 14期

关键词：

D O I：

10.1021/jo00093a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure (S)-(-)-pipecolic acid (5) was synthesized in four steps and 47% overall yield starting from 2-cyano-6-phenyloxazolopiperidine (1). A general strategy is described for preparing 2-alkylated and 6-alkylated pipecolic acid 7a-c and 11a-c using diastereoselective procedures.

引用

页码：3769 / 3774

页数：6

共 34 条

[1] ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES
AGAMI, C
COUTY, F
POURSOULIS, M
VAISSERMANN, J
[J]. TETRAHEDRON, 1992, 48 (03) : 431 - 442
[2] AKETA K, 1976, CHEM PHARM BULL, V24, P621
[3] DEVELOPMENT OF CHIRAL STABILIZED AZOMETHINE YLIDES - A CHIRAL MEMORY RELAY SYSTEM
ANSLOW, AS
HARWOOD, LM
PHILLIPS, H
WATKIN, D
WONG, LF
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1343 - 1358
[4] BAJGROWICZ J, 1986, HETEROCYCLES, V24, P2165
[5] BOCCHI V, 1979, SYNTHESIS-STUTTGART, P961
[6] Bonin M., 1992, ORG SYNTH, V70, P54, DOI DOI 10.15227/ORGSYN.070.0054
[7] SUBSTITUTION OF PROLINE WITH PIPECOLIC ACID AT THE SCISSILE BOND CONVERTS A PEPTIDE SUBSTRATE OF HIV PROTEINASE INTO A SELECTIVE INHIBITOR
COPELAND, TD
WONDRAK, EM
TOZSER, J
ROBERTS, MM
OROSZLAN, S
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 169 (01) : 310 - 314
[8] CONCOMITANT [2,3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC SULFILIMINES AND INTRAMOLECULAR N-ALKYLATION - SYNTHESIS OF 2-VINYL SUBSTITUTED CYCLIC AMINES
DOLLE, RE
LI, CS
SHAW, AN
[J]. TETRAHEDRON LETTERS, 1989, 30 (35) : 4723 - 4726
[9] AN ACYL-IMINIUM ION CYCLIZATION ROUTE TO A NOVEL CONFORMATIONALLY RESTRICTED DIPEPTIDE MIMIC - APPLICATIONS TO ANGIOTENSIN-CONVERTING ENZYME-INHIBITION
FLYNN, GA
GIROUX, EL
DAGE, RC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7914 - 7915
[10] CHIRAL 1,4-DIHYDROPYRIDINE EQUIVALENTS - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALKALOIDS - THE ENANTIOSPECIFIC SYNTHESIS OF (+)-CONIINE AND (-)-CONIINE AND DIHYDROPINIDINE
GUERRIER, L
ROYER, J
GRIERSON, DS
HUSSON, HP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) : 7754 - 7755

← 1 2 3 4 →