Asymmetric synthesis .37. Synthesis of 2,6-disubstituted piperazines from chiral non-racemic lactams

被引：0

作者：

Schanen, V ^{[1
]}

Cherrier, MP ^{[1
]}

deMelo, SJ ^{[1
]}

Quirion, JC ^{[1
]}

Husson, HP ^{[1
]}

机构：

[1] UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CNRS,CHEM THERAPEUT LAB,F-75270 PARIS 06,FRANCE

来源：

SYNTHESIS-STUTTGART | 1996年 / 07期

关键词：

asymmetric synthesis; (R)-(-)-phenylglycinol; 2,6-disubstituted piperazine; metalation of carbamate; alpha-amino acid;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

General and convenient syntheses of optically active 2,6-disubstituted piperazines are described. The method is based on diastereoselective alkylation of lactam 8 derived from (R)-(-)-phenylglycinol followed by a regio- and diastereoselective functionalisation of carbamates 10c and 10d. This procedure allowed the preparation of new alpha-amino acids 15 and 16.

引用

页码：833 / &

页数：6

共 12 条

[1] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES [J].

BEAK, P ;

LEE, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1109-1117

[2] METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].

BEAK, P ;

ZAJDEL, WJ ;

REITZ, DB .

CHEMICAL REVIEWS, 1984, 84 (05) :471-523

[3] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM THE BOC PIPERIDINES [J].

BEAK, P ;

LEE, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2578-2580

[4] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[5]

FALORNI M, 1994, SYNTHESIS-STUTTGART, P391

[6] ASYMMETRIC-SYNTHESIS .36. SYNTHESIS OF TETRAHYDROAZOCINES BY [2+2] THERMAL CYCLOADDITION TO LATENT 1,4-DIHYDROPYRIDINE [J].

LALLEMAND, MC ;

CHIADMI, M ;

TOMAS, A ;

KUNESCH, N ;

HUSSON, HP .

TETRAHEDRON LETTERS, 1995, 36 (12) :2053-2056

[7] ASYMMETRIC-SYNTHESIS OF (2R,6R) AND (2S,6S)-2,6-DIMETHYLPIPERAZINE [J].

MICKELSON, JW ;

JACOBSEN, EJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :19-22

[8] ASYMMETRIC-SYNTHESIS OF 2,6-METHYLATED PIPERAZINES [J].

MICKELSON, JW ;

BELONGA, KL ;

JACOBSEN, EJ .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4177-4183

[9] ASYMMETRIC HYDROGENATION OF TETRAHYDROPYRAZINES - SYNTHESIS OF (S)-PIPERAZINE-2-TERT-BUTYLCARBOXAMIDE, AN INTERMEDIATE IN THE PREPARATION OF THE HIV PROTEASE INHIBITOR INDINAVIR [J].

ROSSEN, K ;

WEISSMAN, SA ;

SAGER, J ;

REAMER, RA ;

ASKIN, D ;

VOLANTE, RP ;

REIDER, PJ .

TETRAHEDRON LETTERS, 1995, 36 (36) :6419-6422

[10] ASYMMETRIC-SYNTHESIS .31. SYNTHESIS OF 2-SUBSTITUTED PIPERAZINES FROM CHIRAL NON-RACEMIC LACTAMS [J].

SCHANEN, V ;

RICHE, C ;

CHIARONI, A ;

QUIRION, JC ;

HUSSON, HP .

TETRAHEDRON LETTERS, 1994, 35 (16) :2533-2536

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