Synthesis of epibatidine isomers: Reductive heck coupling of 2-azabicyclo[2.2.1]hept-5-ene derivatives

被引：36

作者：

Cox, CD ^{[1
]}

Malpass, JR ^{[1
]}

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 40期

关键词：

D O I：

10.1016/S0040-4020(99)00675-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of N-protected 2-azabicyclo[2.2.1]hept-5-enes and 2-chloro-5-iodopyridine under reductive Heck conditions gives approximately equal amounts of exo-5- and exo-6- (6'-chloro-3'-pyridyl)-2-azabicyclo[2.2.1]heptanes. The ratio varies slightly under a range of conditions but both products are isolated in every case (and in the corresponding reaction with 3-iodopyridine) contrary to a recent report that only the 5-exo- isomers are formed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11879 / 11888

页数：10

共 17 条

[1] Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8397-8406

[2] Synthesis of (+/-)-epibatidine and its analogues [J].

Bai, DG ;

Xu, R ;

Chu, GH ;

Zhu, XG .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4600-4606

[3] NMR-STUDIES OF N-METHYL DERIVATIVES OF THE 2-AZABICYCLO [2.2.1]HEPTYL AND 2-AZABICYCLO[2.2.2]OCTYL RING-SYSTEMS - KINETIC PROTONATION IN DETERMINATION OF INVERTOMER PREFERENCES [J].

BELKACEMI, D ;

MALPASS, JR .

TETRAHEDRON, 1993, 49 (40) :9105-9116

[4]

Bencherif M, 1998, J PHARMACOL EXP THER, V284, P886

[5] SYNTHESIS AND MUSCARINIC RECEPTOR ACTIVITY OF ESTER DERIVATIVES OF 2-SUBSTITUTED 2-AZABICYCLO[2.2.1]HEPTAN-5-OL AND 2-ABZABICYCLO[2.2.1]HEPTAN-6-OL [J].

CARROLL, FI ;

ABRAHAM, P ;

CHEMBURKAR, S ;

HE, XC ;

MASCARELLA, SW ;

KWON, YW ;

TRIGGLE, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (12) :2184-2191

[6] A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-EPIBATIDINE [J].

CLAYTON, SC ;

REGAN, AC .

TETRAHEDRON LETTERS, 1993, 34 (46) :7493-7496

[7]

GLENNON RA, 1994, MED CHEM RES, V4, P1

[8] Neuronal nicotinic acetylcholine receptors as targets for drug discovery [J].

Holladay, MW ;

Dart, MJ ;

Lynch, JK .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) :4169-4194

[9] Regiochemistry of the reductive Heck coupling of 2-azabicyclo[2.2.1]hept-5-ene. Synthesis of epibatidine analogues [J].

Kasyan, A ;

Wagner, C ;

Maier, ME .

TETRAHEDRON, 1998, 54 (28) :8047-8054

[10] AZA DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTION - CYCLOCONDENSATION OF DIENES WITH SIMPLE IMINIUM SALTS GENERATED UNDER MANNICH CONDITIONS [J].

LARSEN, SD ;

GRIECO, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1768-1769

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