Stereodefined substituted cyclopropyl zinc reagents from gem-bismetallics

D Beruben, I Marek, JF Normant…

Index: Beruben, Dov; Marek, Ilane; Normant, Jean F.; Platzer, Nicole Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2488 - 2501

Full Text: HTML

Citation Number: 90

Abstract

1, l-or n, nBismetallic reagents bearing a methoxymethyl ether in the y position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes. The nature of the substituents is crucial for this diastereoselection, a n- chelation between one metal and a properly located unsaturation, as well as 1, 2-strain, are proposed to explain the steric outcome of these reactions.

Related Articles:

An improved synthetic preparation of 3-butenal

[Crimmins, Michael T.; Kirincich, Steven J.; Wells, Angela J.; Choy, Allison L. Synthetic Communications, 1998 , vol. 28, # 19 p. 3675 - 3679]

Simple enols. 5.(Z)-and (E)-1-Hydroxy-1, 3-butadiene

[Capon, Brian; Guo, Bozhang Journal of the American Chemical Society, 1988 , vol. 110, # 15 p. 5144 - 5147]

Simple enols. 5.(Z)-and (E)-1-Hydroxy-1, 3-butadiene

[Capon, Brian; Guo, Bozhang Journal of the American Chemical Society, 1988 , vol. 110, # 15 p. 5144 - 5147]

Simple enols. 5.(Z)-and (E)-1-Hydroxy-1, 3-butadiene

[Capon, Brian; Guo, Bozhang Journal of the American Chemical Society, 1988 , vol. 110, # 15 p. 5144 - 5147]

Vinyl ether hydrolysis. XXIX. 1-Methoxy-1, 3-butadiene: reaction mechanism and implication for hydrolysis of the mutagen fecapentaene-12

[Chiang, Yvonne; Eliason, Robert; Guo, Gary H.-X.; Kresge, A. Jerry Canadian Journal of Chemistry, 1994 , vol. 72, # 7 p. 1632 - 1636]

More Articles...