Stereocontrolled synthesis of enantiopure diversely functionalized prototypical piperidinone libraries, and constrained analogs of 4-substituted 2-amino adipic acid

被引：19

作者：

Hanessian, S

Seid, M

Nilsson, I

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

[2] AstraZeneca, Molndal, Sweden

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 11期

基金：

加拿大自然科学与工程研究理事会;

关键词：

sulfonamide; carbamate; piperidine; rigid analogs;

D O I：

10.1016/S0040-4039(02)00183-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure 2-substituted 4.5-unsaturated piperidinones were subjected to stereocontrolled nitroalkane additions and the corresponding products were further manipulated to produce 4-aminomethyl derivatives. Diverse substitution led to a set of 4-arylsulfonamides and O-carbamates as examples of prototypical piperidinone libraries with two sites of diversity. (C) 2002 Elsevier Science Ltd. All rights reserved.

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收藏

页码：1991 / 1994

页数：4

相关论文

共 28 条

[1]

[Anonymous], PIPERIDINES STRUCTUR

[2] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].

Arai, S ;

Nakayama, K ;

Ishida, T ;

Shioiri, T .

TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218

[3] Molecular recognition of protein-ligand complexes: Applications to drug design [J].

Babine, RE ;

Bender, SL .

CHEMICAL REVIEWS, 1997, 97 (05) :1359-1472

[4] DIPOLE-STABILIZED CARBANIONS - THE ALPHA'-LITHIATION OF PIPERIDIDES [J].

BEAK, P ;

ZAJDEL, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1010-1018

[5] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II [J].

BROWN, JD ;

FOLEY, MA ;

COMINS, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7445-7447

[6]

Daly J. W, 1998, The Alkaloids: Chemistry and Biology, V50, P141, DOI 10.1016/S1099-4831(08)60042-5

[7] Convenient preparations of racemic and enantiopure methyl 6-oxopipecolate [J].

Davies, CE ;

Heightman, TD ;

Hermitage, SA ;

Moloney, MG .

SYNTHETIC COMMUNICATIONS, 1996, 26 (04) :687-696

[8]

GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991

[9] N-[(1-BUTYL-4-PIPERIDINYL)METHYL]-3,4-DIHYDRO-2H-[1,3]OXAZINO[3,2-A]INDOLE-10-CARBOXAMIDE HYDROCHLORIDE - THE FIRST POTENT AND SELECTIVE 5-HT4 RECEPTOR ANTAGONIST AMIDE WITH ORAL ACTIVITY [J].

GASTER, LM ;

JOINER, GF ;

KING, FD ;

WYMAN, PA ;

SUTTON, JM ;

BINGHAM, S ;

ELLIS, ES ;

SANGER, GJ ;

WARDLE, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (24) :4760-4763

[10] Towards control of χ-space:: Conformationally constrained analogues of Phe, Tyr, Trp and His [J].

Gibson, SE ;

Guillo, N ;

Tozer, MJ .

TETRAHEDRON, 1999, 55 (03) :585-615