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Synfacts 2010(6): 0711-0711  
DOI: 10.1055/s-0029-1220006
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

TRIP-Catalyzed Asymmetric Addition of Dihydropyrans to N-Acyl Imines

Contributor(s): Benjamin List, Steffen Müller
G. Li, M. J. Kaplan, L. Wojtas, J. C. Antilla*
University of South Florida, Tampa, USA and Sun Yat-Sen University, Guangzhou, P. R. of China
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

A catalytic asymmetric addition of dihydropyrans to N-acyl imines is reported. The authors found, that the chiral phosphoric acid TRIP efficiently promoted the reaction between N-acyl imines and dihydropyrans to give the addition products rather than the as well imaginable [4+2] cycloaddition. With a catalyst loading of 2 mol% the desired addition products were obtained in high yields and good enantioselectivities. Furthermore, the authors submitted some of their products to an MCPA-promoted oxidative cycli­zation furnishing spirocyclic tetrahydropyrans bearing a quaternary stereocenter with perfect ­internal stereocontrol.