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

被引：46

作者：

Kasyan, A

Wagner, C

Maier, ME

机构：

[1] Ukrainian State Univ Chem Technol, UA-320005 Dnepropetrovsk, Ukraine

[2] Univ Halle Wittenberg, Inst Anorgan Chem, D-06120 Halle, Germany

[3] Univ Halle Wittenberg, Inst Organ Chem, D-06120 Halle, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 28期

关键词：

coupling; epibatidine; Diels-Alder reaction;

D O I：

10.1016/S0040-4020(98)00443-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Aider adduct between cyclopentadiene and the iminium salt of formaldehyde was coupled as its boc-derivative with two aryl iodides, The coupling takes place in a regiospecific manner giving the corresponding 5-aryl-2-azabicyclo[2.2.1]heptane derivatives. The structure of the tosyl derivative 8 was established by X-ray analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：8047 / 8054

页数：8

相关论文

共 21 条

[1] Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine [J].

Albertini, E ;

Barco, A ;

Benetti, S ;

DeRisi, C ;

Pollini, GP ;

Zanirato, V .

TETRAHEDRON LETTERS, 1997, 38 (04) :681-684

[2] PALLADIUM-CATALYZED PREPARATION OF EXO-ARYL DERIVATIVES OF THE NORBORNANE SKELETON [J].

ARCADI, A ;

MARINELLI, F ;

BERNOCCHI, E ;

CACCHI, S ;

ORTAR, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) :249-256

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

Bai, DG ;

Xu, R ;

Chu, GH ;

Zhu, XG .

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

[4] Broad-spectrum, non-opioid analgesic activity by selective modulation of neuronal nicotinic acetylcholine receptors [J].

Bannon, AW ;

Decker, MW ;

Holladay, MW ;

Curzon, P ;

Donnelly-Roberts, D ;

Puttfarcken, PS ;

Bitner, RS ;

Diaz, A ;

Dickenson, AH ;

Porsolt, RD ;

Williams, M ;

Arneric, SP .

SCIENCE, 1998, 279 (5347) :77-81

[5] Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]heptanes [J].

Chen, ZM ;

Trudell, ML .

CHEMICAL REVIEWS, 1996, 96 (03) :1179-1193

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

CLAYTON, SC ;

REGAN, AC .

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

[7]

FLETCHER SR, 1994, J ORG CHEM, V59, P771

[8] A diastereospecific synthesis of 2-methyl-5β-phenyl-5α-carbethoxy-2-azabicyclo[2.2.1]heptane:: A ring-constrained analogue of meperidine [J].

Husbands, SM ;

Kline, RH ;

Allen, AC ;

Newman, AH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :418-419

[9] Asymmetric synthesis of epibatidine by use of a novel enantioselective sulfinate elimination reaction [J].

Jones, CD ;

Simpkins, NS ;

Giblin, GMP .

TETRAHEDRON LETTERS, 1998, 39 (09) :1023-1024

[10]

KASYAN A, UNPUB