INVESTIGADORES
KAUFMAN Teodoro Saul
artículos
Título:
Studies on the Intramolecular Oxa-Pictet-Spengler Isomerization of 5-Aryl-1,3-Dioxolanes to 4-Hydroxy-isochromanes
Autor/es:
DARÍO A. BIANCHI; FEDERICO RÚA; TEODORO S. KAUFMAN
Revista:
TETRAHEDRON LETTERS
Editorial:
Elsevier
Referencias:
Lugar: Amsterdam; Año: 2004 vol. 45 p. 411 - 415
ISSN:
0040-4039
Resumen:
The success and stereochemical outcome of the TiCl4-promoted oxa-Pictet?Spengler
cyclization of 5-aryl-1,3-dioxolanes to produce
1,3-disubstituted-4-hydroxy-isochromans, is influenced by the length and nature
of the side chains bound to C-2 and C-4 of the dioxolane. Methyl groups yield a
mixture of 4-hydroxy-isochromans in which the 1,3-trans diastereomer
predominates, while bulkier substituents give 1,3-cis diastereomers.
Functional groups in the C-2 side chain of the dioxolane ring may hinder
cyclization by complexation with the promoter.
