论文信息 - Reinvestigation of the Lewis Acid-mediated Reaction of 3-Aryl-substituted Allyltin Reagents toward Aldehydes. Divergent Stereocontrol of the Product by Lewis Acids

Reinvestigation of the Lewis Acid-mediated Reaction of 3-Aryl-substituted Allyltin Reagents toward Aldehydes. Divergent Stereocontrol of the Product by Lewis Acids

3-Arylallyltin reagents including cinnamyltin stereoselectively gave anti-adducts in the ZnCl2-mediated reaction toward aldehydes in a donating solvent via the 6-membered cyclic transition state. In contrast, the BF3-mediated reaction gave syn-adducts via the acyclic transition state. The present result corrects the previously reported stereochermcal determination of the BF3-mediated product.

A. Takuwa | Y. Nishigaichi

[1] Yoshinori Yamamoto,et al. SELECTIVE REACTIONS USING ALLYLIC METALS , 1993 .

[2] Y. Naruta,et al. Versatile roles of Lewis acids in the reactions of allylic tin compounds , 1993 .

[3] G. Welmaker,et al. (Z)- and (E)-.gamma.-silyloxy allylic stannanes. Highly syn selective reagents for SE' additions to aldehydes , 1992 .

[4] P. Steel,et al. Diastereoselectivity, diastereofacial selectivity and regioselectivity in the reactions of cannamyl chloride with aldehydes mediated by tin and aluminium , 1989 .

[5] P. Steel,et al. Highly diastereoselective reactions of (E)-cinnamyl chloride with aldehydes mediated by tin and aluminium , 1985 .

[6] P. Steel,et al. The stereochemical assignment of the 1,2-diphenylbut-3-en-1-ols, (1RS,2RS,3RS)- and (1RS,2RS,3SR)-3,4-epoxy-1,2-diphenylbutan-1-ols and (2RS,3SR)- and (2RS,3RS)-3,4-epoxy-1,2-diphenylbutan-1-ones and crystal structure of (1RS,2RS,3RS)-3,4-epoxy-1,2-diphenylbutan-1-ol , 1984 .

[7] I. Hamachi,et al. Erythroselectivity in addition of γ-substituted allylsilanes to aldehydes in the presence of titanium chloride , 1983 .

[8] Y. Naruta,et al. Erythro-selective addition of crotyltrialkyltins to aldehydes regardless of the geometry of the crotyl unit. Stereoselection independent of the stereochemistry of precursors , 1980 .