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Synfacts 2011(7): 0716-0716  
DOI: 10.1055/s-0030-1260515
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Camphor-Derived Organocatalytic Synthesis of Chromanones

Contributor(s): Victor Snieckus, Johnathan Board
Z.-Q. Rong, Y. Li, G.-Q. Yang, S.-L. You*
Shanghai Institute of Organic Chemistry and Shenyang University of Chemical Technology, P. R. of China
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

Reported is an organocatalytic Stetter reaction of salicylaldehydes, forming chromanones in high yield and with good enantioselectivity. The catalyst can also be used in other ­organocatalytic reactions, such as benzoin condensations, and may be synthesized in four steps from camphor using well established protocols (Y. Li, Z. Feng, S.-L. You Chem. Commun. 2008, 2263; M. S. Kerr, J. Read de Alaniz, T. Rovis J. Org. Chem. 2005, 70, 5725; Y. K. Chen, S.-J. Jeon, P. J. Walsh, W. A. Nugent Org. Synth. 2005, 82, 87). Due to the good yields and enan­tioselectivities achieved with this catalyst it should find use as an alternative to the already established organocatalysts.