Michael addition versus 1,3-cycloaddition reactions of pyridinium ylides with (arylmethylene)isoxazol-5-ones: Diastereoselective formation of 4-[1-aryl-2-(1-pyridinio)ethyl]isoxazolium-5-olates

DOI: 10.1002/jlac.199719970224

Source and publish data:

Liebigs Annalen p. 441 - 445 (1997)

Update date:2022-08-03

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Authors:

Risitano, Francesco

Grassi, Giovanni

Bruno, Giuseppe

Nicolo, Francesco

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Article abstract of DOI:10.1002/jlac.199719970224

The reactions of (arylmethylene)isoxazol-5-ones 1 with pyridinium ylides 2 lead to the diastereoselective formation of olates 4. The reasons for the favored Michael addition and the unsuccessful subsequent cyclization to fused O-heterocycles are discussed on the basis of X-ray analysis as well as ¹H-NMR and chemical evidences. VCH Verlagsgesellschaft mbH, 1997.

Full text of DOI:10.1002/jlac.199719970224

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