A catalytic asymmetric approach to C-1-chiral 3-methylene-indan-1-ols

作者：Mirabdolbaghi Roya; Dudding Travis^*

来源：Tetrahedron, 2012, 68(7): 1988-1991.

DOI：10.1016/j.tet.2011.12.040

• Asymmetric allylation
• Heck reaction
• Sakurai reaction
• (R)-BINAP
• Sequential catalysis

A sequential (R)-BINAP.(AgF)-F-I (2,2 %26apos;-bis(diphenylphosphino)-1,1 %26apos;-binaphthyl) (6-10 mol %), and (Ph3P)(2)(PdCl2)-Cl-II (bis(triphenylphosphine)palladium(II) dichloride) (2 mol %) catalyzed asymmetric Sakurai-Hosomi-Yamamoto allylation/Mizoroki-Heck reaction that affords C-1-chiral 3-methylene-indan-1-ols with enantiomeric excess (ee) up to 80% is reported. Notably, this protocol allows for the use of various o-substituted benzaldehydes and allyltrimethoxysilane. It was also discovered that the presence of electron-rich groups had no effect on the enantioselectivity of the reaction, whereas electron-withdrawing groups lead to erosion in product ee.

• 出版日期2012-2-18