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Pyrimidine derivativesR 0510 DOI: 10.1002/chin.201008169

Highly Enantioselective Organocatalytic Biginelli and Biginelli-Like Condensa-tions: Reversal of the Stereochemistry by Tuning the 3,3'-Disubstituents of Phos-phoric Acids. — A broad substrate scope of aldehydes and enolizable ketones is tol-erated in the presence of chiral phosphoric acids SPH and PPH. The desired dihydro-pyrimidinethiones are obtained with high enantioselectivities. The change from SPH to PPH affords the opposite enantiomeric products, in most cases with slightly decreased enantioselectivities. Some pharmaceutically interesting compounds and intermediates such as thioureas, dihydropyrimidines, guanidines, and the precursor of the receptor an-tagonist (S)-L-771688 are prepared from the Biginelli products (to be continued). — (LI, N.; CHEN, X.-H.; SONG, J.; LUO, S.-W.; FAN, W.; GONG*, L.-Z.; J. Am. Chem. Soc. 131 (2009) 42, 15301-15305; Chengdu Inst. Org. Chem., Chin. Acad. Sci., Chengdu 610041, Peop. Rep. China; Eng.) — Klein

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ChemInform 2010, 41, issue 08 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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ChemInform 2010, 41, issue 08 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim