Use of metallated allylic ethers for the elaboration of vicinally trisubstituted linear substrates or cyclopropyl carbinols

作者: Franck Ferreira , Christelle Herse , Eric Riguet , Jean F Normant

DOI: 10.1016/S0040-4039(00)00025-3

关键词: ReagentCyclopropanationZincAllylic rearrangementChemistryOrganic chemistry

摘要: Abstract Allyl zinc reagents derived from allylic ethers carbometallate vinyllithiums secondary ethers, leading to linear 3,5-dialkoxy-4-methyl-1-alkenes, or 1-vinyl-2-alkoxyalkyl cyclopropanes diastereoselectively.

参考文章(6)
Ilane Marek, Jean-Michel Lefrançois, Jean-F. Normant, Iodocyclization of olefinic t-butyl ethers : an easy stereocontrolled synthesis of cis-substituted tetrahydrofurans. Tetrahedron Letters. ,vol. 33, pp. 1747- 1748 ,(1992) , 10.1016/S0040-4039(00)91722-2
Dov Beruben, Ilane Marek, Jean F. Normant, Nicole Platzer, Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics Journal of Organic Chemistry. ,vol. 60, pp. 2488- 2501 ,(1995) , 10.1021/JO00113A032
Andre B. Charette, Helene Lebel, Diastereoselective Cyclopropanation of Chiral Allylic Alcohols: A More Efficient Reagent for the Relative Stereocontrol Journal of Organic Chemistry. ,vol. 60, pp. 2966- 2967 ,(1995) , 10.1021/JO00115A008
D. A. Evans, G. C. Andrews, B. Buckwalter, Metalated allylic ethers as homoenolate anion equivalents Journal of the American Chemical Society. ,vol. 96, pp. 5560- 5561 ,(1974) , 10.1021/JA00824A039
Ilane Marek, Jean-Michel Lefrancois, Jean-F. Normant, Diastereoselective Carbometalation of Vinyl Metals Journal of Organic Chemistry. ,vol. 59, pp. 4154- 4161 ,(1994) , 10.1021/JO00094A028