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Chemistry. 2013 Jul 22;19(30):9754-9. doi: 10.1002/chem.201301039. Epub 2013 Jul 5.

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

Author information

1
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

Abstract

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).

KEYWORDS:

Diels-Alder reactions; asymmetric catalysis; calcium phosphate; chirality; fused indoles

PMID:
23832817
DOI:
10.1002/chem.201301039
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