Synthesis of new quinuclidine derivatives via Pd-mediated cross-coupling and cross-benzannulation reactions

被引：3

作者：

Totos, Stefania ^{[1
,2
]}

Fild, Manfred ^{[2
]}

Thoene, Carsten ^{[2
]}

Grosu, Ion ^{[3
]}

机构：

[1] Univ Babes Bolyai, Raluca Raipan Inst Res Chem, Cluj Napoca 400294, Romania

[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Anorgan & Analyt Chem, D-38106 Braunschweig, Germany

[3] Univ Babes Bolyai, Fac Chem & Chem Engn, Cluj Napoca 400028, Romania

来源：

TETRAHEDRON | 2009年 / 65卷 / 31期

关键词：

CATALYZED CYCLOTRIMERIZATION; MOLECULAR-MECHANICS; CINCHONA ALKALOIDS; CONJUGATED ENYNES; ALKYNES; ENANTIOSELECTIVITY; DIHYDROXYLATION; QUINCORINE; COMPLEXES; ADDITIONS;

D O I：

10.1016/j.tet.2009.05.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New functionalized quinuclidines were prepared via palladium-catalyzed addition reactions of terminal alkynes (donors) to internal alkynes (acceptors). The enantiopure terminal alkynes were derivatives of quincoridine and quincorine, two semi-natural Cinchona alkaloids. The processes exhibited high chemoselectivity and excellent diastereoselectivity, the E-enynes being obtained as single products in almost all cases. The synthesis of new tetra and pentasubstituted benzene derivatives in good yields by [2+2+2] benzannulation of the diynes, obtained by the palladium-catalyzed homodimerization of 10,11-didehydro quincoridine and 10,11-didehydro quincorine, with terminal alkynes and in fair yield by [4+2] benzannulation of an enyne derivative of 10,11-didehydro quincoridine with 2,4-hexane-diyne are reported. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6226 / 6235

页数：10

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