The first example of enamine-Lewis acid cooperative bifunctional catalysis: application to the asymmetric aldol reaction

Chemical Communications : Chem Comm
Kenny ArnoldKerstin Zawatzky

Abstract

(-)-Sparteine directed lithiation of N-Boc-pyrrolidine, alkylation with chloromethylboronate pinacol ester and acid-based deprotection provides homoboroproline HX salt in 94% ee, which is then an efficient enamine-type pyrrolidine catalyst in an asymmetric aldol reaction when neutralised and especially when esterified in situ with a tartrate ester, for example, providing 90% ee of the aldol adduct derived from acetone and p-nitrobenzaldehyde.

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Citations

Apr 1, 2011·The Journal of Organic Chemistry·Jing SunWebster L Santos
May 3, 2018·Chemistry, an Asian Journal·Bin Rao, Rei Kinjo
May 19, 2018·Organic & Biomolecular Chemistry·Man-Yi HanLei Wang
Mar 29, 2014·Chemistry, an Asian Journal·Andrea GualandiPier Giorgio Cozzi
Jan 18, 2017·Angewandte Chemie·Ana VarelaVarinder K Aggarwal
Nov 26, 2019·Topics in Current Chemistry·Pier Giorgio CozziGiacomo Rodeghiero
Apr 18, 2009·Accounts of Chemical Research·Irene GeorgiouAndrew Whiting
Jun 6, 2012·Journal of the American Chemical Society·Zhi HeAndrei K Yudin
May 23, 2018·The Journal of Organic Chemistry·Henry S RzepaTom D Sheppard
Sep 30, 2021·Chemical Society Reviews·Wenbo MingTodd B Marder

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