Studies on the intramolecular oxa-Pictet–Spengler rearrangement of 5-aryl-1, 3-dioxolanes to 4-hydroxy-isochromans

DA Bianchi, F Rúa, TS Kaufman

Index: Bianchi, Dario A.; Rua, Federico; Kaufman, Teodoro S. Tetrahedron Letters, 2004 , vol. 45, # 2 p. 411 - 415

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Citation Number: 39

Abstract

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. ...