Diastereo- and enantioselective carbolithiation of allyl o-lithloaryl ethers.: New chiral cyclopropane derivatives

被引:36
作者
Barluenga, J
Fañanás, FJ
Sanz, R
Marcos, C
机构
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, CSIC, Unidad Asociada, Oviedo 33701, Spain
[2] Univ Burgos, Dept Quim, Fac Ciencias, Area Quim Organ, Burgos 09001, Spain
关键词
D O I
10.1021/ol026078x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Different allyl 2-lithloaryl ethers undergo a tandem carbolithiation/gamma-elimination in Et2O/TMEDA affording o-cyclopropyl phenol or naphthol derivatives in a diastereoselective manner. The use of (-)-sparteine as a chiral ligand instead of TMEDA allows the synthesis of cyclopropane derivatives with up 81% ee.
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页码:2225 / 2228
页数:4
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