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Issue 11, 1995
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Chemoselectivity and stereoselectivity of cyclisation of α-diazocarbonyls leading to oxygen and sulfur heterocycles catalysed by chiral rhodium and copper catalysts

Abstract

Good levels of enantioselectivity have been achieved in intramolecular C–H insertion reactions of α-diazocarbonyl compounds leading to six-membered oxygen heterocycles (chromanones) through the use of chiral rhodium(II) carboxylates as catalysts. Competition between C–H insertion and sigmatropic rearrangement, the latter leading to five-membered oxygen heterocycles (furanones), was observed with precursors containing a proximal O-allyl side chain. Whereas rhodium carboxylates produced C-H insertion products predominantly, a copper catalyst produced sigmatropic rearrangement products exclusively. A precursor with an S-allyl side chain exhibited cyclisation via sigmatropic rearrangement with both copper and rhodium catalysts.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1995, 1373-1379
Article type
Paper

Chemoselectivity and stereoselectivity of cyclisation of α-diazocarbonyls leading to oxygen and sulfur heterocycles catalysed by chiral rhodium and copper catalysts

T. Ye, C. F. García and M. A. McKervey, J. Chem. Soc., Perkin Trans. 1, 1995, 1373
DOI: 10.1039/P19950001373

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