Tetrahedron

Stereo-and regiocontrol of acyclic systems via the lewis acid mediated reaction of allylic stannanes with aldehydes

Y Yamamoto, H Yatagai, Y Ishihara, N Maeda…

文献索引：Yamamoto, Yoshinori; Yatagai, Hidetaka; Ishihara, Yuji; Maeda, Norihiko; Maruyama, Kazuhiro Tetrahedron, 1984 , vol. 40, # 12 p. 2239 - 2246

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被引用次数: 178

摘要

The reaction of crotyltrialkylstannanes (1) with aldehydes in the presence of BF3, OEt2, produces the corresponding erythro homoallyl alcohols (2) predominantly regardless of the geometry of the double bond. Further, the Lewis acid mediated reaction exhibits the enhanced Cram selectivity in comparison with other allylic organometallic reactions which proceed in the absence of Lewis acids. Use of AlCl3-i-PrOH as the Lewis acid entirely ...