CONSTRUCTION OF CHIRAL 2-FUNCTIONALIZED PIPERIDINE VIA ENZYMATIC RESOLUTION AND PALLADIUM-CATALYZED N-ALKYLATION

被引：45

作者：

HIRAI, Y

NAGATSU, M

机构：

来源：

CHEMISTRY LETTERS | 1994年 / 01期

关键词：

D O I：

10.1246/cl.1994.21

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The palladium-catalyzed cyclization of the optically active urethan [(-)-1], which was obtained by enzymatic resolution of the racemic alcohol (1), gave the piperidine 6. This reaction affords highly efficient intramolecular chirality transfer. Compound 6 was converted into (+)-coniine and 2-hydroxymethylpiperidine.

引用

收藏

页码：21 / 22

页数：2

相关论文

共 19 条

[1]

AKETA K, 1976, CHEM PHARM BULL, V24, P621

[2] CONVERSION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES TO 4-CHLORO-1,2-DIHYDROPYRIDINES USING THE VILSMEIER REAGENT [J].

ALAWAR, RS ;

JOSEPH, SP ;

COMINS, DL .

TETRAHEDRON LETTERS, 1992, 33 (50) :7635-7638

[3] ASYMMETRIC REDUCTION OF IMINES WITH LITHIUM BUTYL(HYDRO)DIPINAN-3ALPHA-YL-BORATE AND RELATED REAGENTS [J].

ARCHER, JF ;

BOYD, DR ;

JACKSON, WR ;

GRUNDON, MF ;

KHAN, WA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (14) :2560-&

[4] ENZYME-MEDIATED ENANTIOSELECTIVE ACYLATION OF SECONDARY-AMINES IN ORGANIC-SOLVENTS [J].

ASENSIO, G ;

ANDREU, C ;

MARCO, JA .

TETRAHEDRON LETTERS, 1991, 32 (33) :4197-4198

[5]

BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049

[6] IODOCYCLIZATION OF ALLYLIC ALCOHOL DERIVATIVES CONTAINING INTERNAL NUCLEOPHILES - CONTROL OF STEREOSELECTIVITY BY SUBSTITUENTS IN THE ACYCLIC PRECURSORS [J].

CHAMBERLIN, AR ;

DEZUBE, M ;

DUSSAULT, P ;

MCMILLS, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5819-5825

[7] CHIRAL 1,4-DIHYDROPYRIDINE EQUIVALENTS - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALKALOIDS - THE ENANTIOSPECIFIC SYNTHESIS OF (+)-CONIINE AND (-)-CONIINE AND DIHYDROPINIDINE [J].

GUERRIER, L ;

ROYER, J ;

GRIERSON, DS ;

HUSSON, HP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7754-7755

[8]

Heck R. F., 1985, PALLADIUM REAGENTS O

[9] AN EFFICIENT SYNTHESIS OF (-)-BULGECININE [J].

HIRAI, Y ;

TERADA, T ;

AMEMIYA, Y ;

MOMOSE, T .

TETRAHEDRON LETTERS, 1992, 33 (51) :7893-7894

[10] DIASTEREOFACIAL SELECTIVITY IN INTERMOLECULAR NITRONE CYCLOADDITIONS TO CHIRAL ALLYL ETHERS - APPLICATION TO CHIRAL SYNTHESIS OF CONIINE [J].

ITO, M ;

MAEDA, M ;

KIBAYASHI, C .

TETRAHEDRON LETTERS, 1992, 33 (26) :3765-3768