2016年4月4日月曜日

Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles - Ohmiya - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles - Ohmiya - 2016 - Angewandte Chemie International Edition - Wiley Online Library


Abstract

Copper-catalyzed enantioselective allylic alkylation of azoles
with γ,γ-disubstituted primary allylic phosphates was achieved using a
new chiral N-heterocyclic carbene ligand bearing a naphtholic hydroxy
group. This reaction occurred with excellent branch regioselectivity and
high enantioselectivity, thus forming a controlled all-carbon
quaternary stereogenic center at the position α to the heteroaromatic
ring.
Thumbnail image of graphical abstract
Branch out: The title reaction proceeds with
γ,γ-disubstituted primary allylic phosphates and a new chiral
N-heterocyclic carbene ligand bearing a naphtholic hydroxy group. The
reaction occurs with excellent branch regioselectivity and high
enantioselectivity, thus forming a controlled all-carbon quaternary
stereogenic center at the position α to the heteroaromatic ring.

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