PALLADIUM-CATALYZED REDUCTION OF AN ALLYLIC AMINE - A FORMAL ACCESS TO BOTH DIASTEREOISOMERS OF CYCLOPENTENYL GLYCINE

被引：16

作者：

BOURGEOISCURY, A

DOAN, D

GORE, J

机构：

[1] Laboratoire de Chimie Organique 1, associé au CNRS, Université Claude Bernard, 69622 Villeurbanne, 43 Bd du

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)91600-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The easily accessible bicyclic amines 3 (exo or endo) are regioselectively transformed to the methyl esters of the diastereoisomers (1c or 1d) of N-benzyl cyclopentenyl glycine by reaction with hydride donors (mainly NaBH3CN) in the presence of a palladium(0) catalyst.

引用

页码：1277 / 1280

页数：4

共 11 条

[1] AZA DIELS-ALDER REACTIONS IN WATER - CYCLOCONDENSATION OF C-ACYL IMINIUM IONS WITH CYCLOPENTADIENE [J].

GRIECO, PA ;

LARSEN, SD ;

FOBARE, WF .

TETRAHEDRON LETTERS, 1986, 27 (18) :1975-1978

[2]

GRIECO PA, 1985, J AM CHEM SOC, V107, P1768

[3] PREPARATION AND RESOLUTION OF CYCLOPENTANEGLYCINE [J].

HILL, JT ;

DUNN, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1321-&

[4] ORGANO TIN NUCLEOPHILES .3. PALLADIUM CATALYZED REDUCTIVE CLEAVAGE OF ALLYLIC HETEROSUBSTITUENTS WITH TIN HYDRIDE [J].

KEINAN, E ;

GREENSPOON, N .

TETRAHEDRON LETTERS, 1982, 23 (02) :241-244

[5] A PRACTICAL SYNTHESIS OF MYRCENOL BY PALLADIUM COMPLEX - CATALYZED ELIMINATION-REACTION [J].

KUMOBAYASHI, H ;

MITSUHASHI, S ;

AKUTAGAWA, S ;

OHTSUKA, S .

CHEMISTRY LETTERS, 1986, (02) :157-160

[6] IMINO DIELS-ALDER CYCLOADDITIONS - AN APPLICATION TO THE SYNTHESIS OF (+/-)-ARISTEROMYCIN [J].

MAGGINI, M ;

PRATO, M ;

SCORRANO, G .

TETRAHEDRON LETTERS, 1990, 31 (43) :6243-6246

[7] PALLADIUM-CATALYZED SELECTIVE HYDROGENOLYSIS OF ALKENYLOXIRANES WITH FORMIC-ACID - STEREOSELECTIVITY AND SYNTHETIC UTILITY [J].

OSHIMA, M ;

YAMAZAKI, H ;

SHIMIZU, I ;

NISAR, M ;

TSUJI, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6280-6287

[8]

SANTOSO S, 1981, LIEBIGS ANN CHEM, V658

[9] ASYMMETRIC AZA-DIELS-ALDER REACTION USING THE CHIRAL 1-PHENYL-ETHYL IMINE OF METHYL GLYOXYLATE [J].

STELLA, L ;

ABRAHAM, H ;

FENEAUDUPONT, J ;

TINANT, B ;

DECLERCQ, JP .

TETRAHEDRON LETTERS, 1990, 31 (18) :2603-2606

[10] PYRROLE ANNULATION ONTO ALDEHYDES AND KETONES VIA PALLADIUM-CATALYZED REACTIONS [J].

TROST, BM ;

KEINAN, E .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (14) :2741-2746

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