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…

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

Full Text: HTML

Citation Number: 178

Abstract

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 ...

Related Articles:

A detailed investigation of the aza-Prins reaction

[Dobbs, Adrian P.; Guesne, Sebastien J. J.; Parker, Robert J.; Skidmore, John; Stephenson, Richard A.; Hursthouse, Mike B. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 5 p. 1064 - 1080]

Transition metal promoted alkylations of unsaturated alcohols: the selective methylation of homopropargyl alcohols via titanium tetrachloride-trimethylaluminum

[Ewing, James C.; Ferguson, Gregory S.; Moore, Douglas W.; Schultz, Frederick W.; Thompson, David W. Journal of Organic Chemistry, 1985 , vol. 50, # 12 p. 2124 - 2128]

TITANIUM-MEDIATED AND NEIGHBORING-GROUP ASSISTED δ-METHYLATION OF HOMOALLYL ALCOHOLS: A NEW REGIO-AND STEREOSELECTIVE CC- …

[Fujita, Katsuramaru; Moret, Etienne; Schlosser, Manfred Chemistry Letters, 1982 , p. 1819 - 1822]

More Articles...