Nickel-Catalyzed Double Bond Transposition of Alkenyl Boronates for in Situ syn-Selective Allylboration Reactions

Organic Letters
Felicia WeberGerhard Hilt

Abstract

The transposition of a homoallyl pinacol boronic ester was realized by a highly reactive nickel-catalyst system comprising NiCl2(dppp), zinc powder, ZnI2, and Ph2PH. The in situ generated Z-crotyl pinacol boronic esters were reacted with various aldehydes to form syn-homoallylic alcohols in high diastereoselectivities. The present nickel-catalyzed reaction is complementary to the iridium-catalyzed transposition reported by Murakami leading to the corresponding anti-homoallylic alcohols. Also, the multiple transposition of pentenyl pinacol boronic ester was realized.

References

May 1, 2008·Chemistry : a European Journal·Jörg PietruszkaLi Grundl
May 16, 2009·The Journal of Organic Chemistry·Hwan Jung LimT V RajanBabu
Oct 7, 2011·Angewandte Chemie·Hiroshi ShimizuMasahiro Murakami
Jan 5, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Nanna AhlstenBelén Martín-Matute
Jun 19, 2012·Journal of the American Chemical Society·Casey R Larsen, Douglas B Grotjahn
Feb 23, 2013·Journal of the American Chemical Society·Joseph R ClarkSteven T Diver
Aug 1, 2013·Chemical Communications : Chem Comm·Lu WangAiwen Lei
Jan 7, 2014·Journal of the American Chemical Society·Chi ChenPatrick L Holland
Jan 16, 2014·Journal of the American Chemical Society·Casey R LarsenDouglas B Grotjahn
Apr 17, 2014·Journal of the American Chemical Society·Tomoya MiuraMasahiro Murakami

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