ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION OF IMINES WITH DIENES

被引：66

作者：

BAILEY, PD ^{[1
]}

WILSON, RD ^{[1
]}

BROWN, GR ^{[1
]}

机构：

[1] ICI PLC,PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 05期

关键词：

D O I：

10.1039/p19910001337

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active pipecolic acid derivatives can be prepared by the aza-Diels-Alder reaction of simple dienes with the imine derived from ethyl glyoxylate and chiral 1-phenylethylamine; the cycloadditions are regiospecific, highly diastereoselective within the heterocyclic ring (> 92% exo with cyclic dienes, and 100% endo with acyclic dienes), and lead to high asymmetric induction in most cases (average d.e. = 72%).

引用

页码：1337 / 1340

页数：4

共 27 条

[1]

AARON HS, 1979, TOP STEREOCHEM, V11, P34

[2] HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE [J].

ALBRECHT, R ;

KRESZE, G .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1431-&

[3]

BOGER DL, 1987, HETERO DIELSALDER ME

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .6. HYDROBORATION .74. ASYMMETRIC HYDROBORATION OF REPRESENTATIVE HETEROCYCLIC OLEFINS WITH DIISOPINOCAMPHEYLBORANE - SYNTHESIS OF HETEROCYCLIC BORONATES AND HETEROCYCLIC ALCOHOLS OF VERY HIGH ENANTIOMERIC PURITY [J].

BROWN, HC ;

PRASAD, JVNV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2049-2054

[5] 2-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID - A BICYCLIC PROLINE [J].

GAITANOPOULOS, DE ;

WEINSTOCK, J .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (04) :957-959

[6] 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

[7]

Hamer J., 1967, 1 4 CYCLOADDITION RE

[8] STEREOSELECTIVE DELTA-4-PIPECOLIC ACID SYNTHESIS VIA ALKYLATION OF A VINYL N-BOC-IMINIUM ION DERIVED FROM BAIKIAIN [J].

HANSON, GJ ;

RUSSELL, MA .

TETRAHEDRON LETTERS, 1989, 30 (42) :5751-5754

[9]

HOLMES AB, 1988, J CHEM SOC CHEM COMM, P1599

[10] A SIMPLE AND EFFICIENT SYNTHESIS OF ETHYL AND METHYL GLYOXYLATE [J].

HOOK, JM .

SYNTHETIC COMMUNICATIONS, 1984, 14 (01) :83-87

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