Ti-Mediated Tandem Ethylation and Functionalization of Allylic
Alcohols

doi:10.1055/s-0031-1289344

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Synfacts 2011(12): 1353-1353
DOI: 10.1055/s-0031-1289344

Metal-Mediated Synthesis

Ti-Mediated Tandem Ethylation and Functionalization of Allylic Alcohols

Contributor(s): Paul Knochel, Andreas K. Steib
P. P. Das, I. L. Lysenko, J. K. Cha*
Wayne State University, Detroit, USA

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Publication History

Publication Date:
18 November 2011 (online)

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Significance

A new stereoselective alkylation of allylic alcohols by trapping of the presumed organometallic intermediates with suitable electrophiles has been disclosed. This titanium-mediated reaction proceeds in an S_N2′ manner and uses EtMgBr as alkylation reagent and ClTi(Oi-Pr)₃ as scavenger for magnesium alkoxides.