Lewis Acid-Promoted Enantioselective Dearomative Spirocyclizations of Allenes

The Journal of Organic Chemistry
Sergei TcyrulnikovMarisa C Kozlowski

Abstract

A chiral oxazaborolidine combined with SnCl4 has been found to promote the dearomative spirocyclization of electron-rich benzyl allenyl ketones. The reaction outcome is sensitive to the nature of activating acid, which was rationalized using hard-soft acid-base (HSAB) theory. The spirocyclic product was obtained with up to 72% ee, which is the best result reported to date for these substrates. The formation of cross-conjugated or conjugated products is readily controlled by changing the oxygen-protecting groups.

References

Apr 11, 2002·Journal of the American Chemical Society·E J CoreyThomas W Lee
Jan 22, 2011·The Journal of Organic Chemistry·Jacob Y ChaThomas R R Pettus
Oct 14, 2011·Organic Letters·Elisa G GutierrezAnnaliese K Franz
Apr 24, 2012·Chemical Reviews·Timothy S De VriesEdwin Vedejs
Jun 22, 2013·Organic Letters·William P UnsworthRichard J K Taylor
Dec 3, 2016·Organic & Biomolecular Chemistry·Aimee K ClarkeWilliam P Unsworth
Dec 13, 2016·Chemical Reviews·Man-Cheng TangYi Tang
Oct 25, 2017·Chemical Reviews·Benjamin K Liebov, W Dean Harman

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