Intramolecular carbolithiation of allyl o-lithioaryl ethers:: A new enantioselective synthesis of functionalized 2,3-dihydrobenzofurans

被引：43

作者：

Barluenga, J

Fañanás, FJ

Sanz, R

Marcos, C

机构：

[1] Univ Oviedo, CSIC, Unidad Asociada, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

[2] Univ Burgos, Fac Ciencias, Area Quim Organ, Dept Quim, Burgos 09001, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 18期

关键词：

(-)-sparteine; 2,3-dihydrobenzofurans; allyl aryl ethers; enantioselectivity; intramolecular carbolithiation; synthetic methods;

D O I：

10.1002/chem.200500377

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new and easy method for the diastereoselective synthesis of 3-functionalized 2,3-dihydrobenzofuran derivatives from allyl 2-bromoaryl ethers is described. The key step of this transformation involves an intramolecular carbolithiation reaction of allyl 2-lithioaryl ethers. The substituents in both the allyl and the aryl moieties play an important and decisive role in stopping the reaction at the benzofuran thus avoiding a gamma-elimination reaction. Finally, this process is amenable to the synthesis of enantiornerically enriched compounds by using (-)-sparteine as a chiral inductor.

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页码：5397 / 5407

页数：11

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