Stereochemistry of the cyclotrimerisation of enantiopure polycyclic bromostannylalkenes: Mechanistic considerations on the coupling of alkenyl stannanes by copper(II) nitrate

被引:27
作者
Zonta, C [1 ]
Cossu, S [1 ]
Peluso, P [1 ]
De Lucchi, O [1 ]
机构
[1] Univ Venice, Dipartimento Chim, I-30123 Venice, Italy
关键词
stereoselection; coupling reactions; mechanisms; copper and compounds;
D O I
10.1016/S0040-4039(99)01736-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclotrimerisation of enantiopure 1-bromo-2-trimethylstannylbenzonorbornadiene 2, contrary to the expectations, affords predominantly the trimer anti-4. This observation suggests that the reaction proceeds mainly via a Sn-Sn coupling to produce the dimer anti-5 and a tin-copper product that triggers halogen-metal exchange on the dimer thus allowing a second coupling with the starling reagent eventually leading to the anti-trimer. The little hut consistent formation of the isomer syn-4 and meso dimer 5 can arise from a racemisation of the bromine-copper-tin intermediate possibly via an alkyne structure. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8185 / 8188
页数:4
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