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Enantioselective construction of dihydropyran-fused indoles through chiral calcium phosphate catalyzed oxo-hetero-Diels-Alder reactions by using 2-oxoindolin-3-ylidenes as heterodienes

Enantioselective construction of dihydropyran-fused indoles through chiral calcium phosphate catalyzed oxo-hetero-Diels-Alder reactions by using 2-oxoindolin-3-ylidenes as heterodienes

Chemistry 19(30): 9754-9759

Carbon-carbon bond formation: A highly efficient method for the oxo-hetero-Diels-Alder reaction of 2-oxoindolin-3-ylidenes based on chiral calcium phosphate is described. In general, adducts were obtained with high yields and excellent diastereo- and enantioselectivities (up to 96 % yield, >99:1 endo/exo, >99 % ee; see scheme, Boc = tert-butoxycarbonyl).

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Accession: 052954151

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PMID: 23832817

DOI: 10.1002/chem.201301039

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