Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide

Chemistry : a European Journal
Fuxue ChenYaozhong Jiang

Abstract

Double-activation catalysis promises high catalytic efficiency in the enantioselective cyanosilylation of ketones through the combined use of a Lewis acid and a Lewis base. Catalyst systems composed of a chiral salen-Al complex and an N-oxide have high catalytic turnovers (200 for aromatic ketones, 1000 for aliphatic ones). With these catalysts, a wide range of aliphatic and aromatic ketones were converted under mild conditions into tertiary cyanohydrin O-TMS ethers in excellent yields and with high enantioselectivities (94% ee for aromatic ketones, 90% ee for aliphatic ones). Preliminary mechanistic studies revealed that the salen-Al complex played the role of a Lewis acid to activate the ketone and the N-oxide that of a Lewis base to activate TMSCN; that is, double activation.

Citations

Jul 21, 2017·Organic Letters·Jiashen QiuFu-Xue Chen
Nov 20, 2014·Organic & Biomolecular Chemistry·Yao-Feng WangFu-Xue Chen
Apr 7, 2010·Chemical Communications : Chem Comm·Robert M HaakArjan W Kleij
May 6, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea GualandiPier Giorgio Cozzi
Jan 18, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·J TernelR M Gauvin
Apr 21, 2012·Chemical Science·Anna E Allen, David W C Macmillan
May 8, 2008·The Journal of Organic Chemistry·David BernierSimon Woodward
Apr 28, 2009·The Journal of Organic Chemistry·Seb CailleMargaret M Faul
Dec 11, 2008·Chemical Reviews·Michael NorthCarl Young
Apr 12, 2013·Organic Letters·Brad M LoertscherSteven L Castle
Jun 21, 2007·The Journal of Physical Chemistry. a·Séverine MarquisHermenegildo Garcia

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