A simple and scalable method to prepare 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane

被引：12

作者：

Yang, CH ^{[1
]}

Jensen, MS ^{[1
]}

Conlon, DA ^{[1
]}

Yasuda, N ^{[1
]}

Hughes, DL ^{[1
]}

机构：

[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 45期

关键词：

tin and compounds; bicyclic heterocyclic compounds; coupling reagents;

D O I：

10.1016/S0040-4039(00)01570-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and scalable method for the preparation of a potentially versatile organostannane, 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane (1), is described. Stannane 1 was prepared by the disproportionation of N(CH2CH2CH2SnBu3)(3) and SnCl4 at 70-100 degreesC. This reaction requires the addition of water or an alcohol to proceed efficiently. Under typical conditions, 1 was isolated in 50-55% yield after a simple acid/base extraction sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：8677 / 8681

页数：5

相关论文

共 8 条

[1] STEREOGNOSTIC COORDINATION CHEMISTRY .1. THE DESIGN AND SYNTHESIS OF CHELATORS FOR THE URANYL-ION [J].

FRANCZYK, TS ;

CZERWINSKI, KR ;

RAYMOND, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8138-8146

[2]

HAHN FE, 1991, CHEM BER, V124, P481

[3] Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling [J].

Jensen, MS ;

Yang, CH ;

Hsiao, Y ;

Rivera, N ;

Wells, KM ;

Chung, JYL ;

Yasuda, N ;

Hughes, DL ;

Reider, PJ .

ORGANIC LETTERS, 2000, 2 (08) :1081-1084

[4] STRUCTURE AND REACTIVITY OF STANNYLATED PROPYL AMINES AND PROPYL SULFIDES - CRYSTAL AND MOLECULAR-STRUCTURE OF BIS(3-CHLORODIMETHYLSTANNYLPROPYL)SULFIDE S(CH2CH2CH2SNME2CL)2 [J].

JURKSCHAT, K ;

SCHMID, B ;

DYBIONA, M ;

BAUMEISTER, U ;

HARTUNG, H ;

TZSCHACH, A .

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1988, 560 (05) :110-118

[5] Heterogeneous palladium-catalyzed regioselective hydrostannation of alkenes [J].

Lautens, M ;

Kumanovic, S ;

Meyer, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (12) :1329-1330

[6] NMR INVESTIGATIONS ON STANNABICYCLOUNDECANES OF THE TYPE RSN(CH2CH2CH2)3N [J].

MUGGE, C ;

PEPERMANS, H ;

GIELEN, M ;

WILLEM, R ;

TZSCHACH, A ;

JURKSCHAT, K .

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1988, 567 (12) :122-130

[7] PENTACOORDINATED TETRAORGANOTIN AND SILICON-COMPOUNDS - SYNTHESIS AND STRUCTURES [J].

TZSCHACH, A ;

JURKSCHAT, K .

PURE AND APPLIED CHEMISTRY, 1986, 58 (04) :639-646

[8] INTERNAL COORDINATION AT TIN PROMOTES SELECTIVE ALKYL TRANSFER IN THE STILLE COUPLING REACTION [J].

VEDEJS, E ;

HAIGHT, AR ;

MOSS, WO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6556-6558