Asymmetric 1,3-dipolar cycloadditions of N-benzyl and N-diphenylmethyl nitrones and alpha,beta-unsaturated aldehydes catalyzed by bis-titanium chiral Lewis acids

Chemistry, an Asian Journal
Takuya HashimotoKeiji Maruoka

Abstract

Bis-titanium chiral Lewis acids that contain two oxygen-bridged titanium centers were successfully applied to the asymmetric 1,3-dipolar cycloaddition of nitrones and alpha,beta-unsaturated aldehydes. The introduction of the diphenylmethyl group as the N substituent on the nitrones, with the aim of destabilizing the nitrone-Lewis acid complex, led to the drastic enhancement of not only the reactivity but also the enantioselectivity. By employing this approach, 1,3-dipolar cycloadditions of nitrones and the rather unreactive methacrolein were facilitated to give cycloadducts that bear one all-carbon quaternary center with unique regioselectivity and excellent stereoselectivity.

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Citations

Dec 5, 2012·The Journal of Organic Chemistry·Nemai Saha, Shital K Chattopadhyay
Mar 5, 2010·Journal of the American Chemical Society·Takuya HashimotoKeiji Maruoka
Dec 17, 2016·Chemical Reviews·Mathéo BerthetJean Martinez
Jun 20, 2008·Organic & Biomolecular Chemistry·Takuya HashimotoKeiji Maruoka
Nov 1, 2011·Organic & Biomolecular Chemistry·Andrei Bădoiu, E Peter Kündig
Jul 23, 2013·Journal of the American Chemical Society·Takuya HashimotoKeiji Maruoka
May 12, 2015·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Dec 7, 2018·The Journal of Organic Chemistry·Makoto SakoHiroaki Sasai

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