Palladium-catalyzed domino C-C/C-N coupling using a norbornene template: synthesis of substituted benzomorpholines, phenoxazines, and dihydrodibenzoxazepines

Praew Thansandote; Eugene Chong; Kai-Oliver Feldmann; Mark Lautens

doi:10.1021/jo100408p

Palladium-catalyzed domino C-C/C-N coupling using a norbornene template: synthesis of substituted benzomorpholines, phenoxazines, and dihydrodibenzoxazepines

J Org Chem. 2010 May 21;75(10):3495-8. doi: 10.1021/jo100408p.

Authors

Praew Thansandote¹, Eugene Chong, Kai-Oliver Feldmann, Mark Lautens

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

PMID: 20423091
DOI: 10.1021/jo100408p

Abstract

A rapid, four-step approach to alkyl- and aryl-substituted benzomorpholines is accomplished by a Pd-catalyzed domino C-C/C-N bond coupling using a norbornene template. Extension to phenoxazines and dihydrodibenzoxazepines is presented.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzoxazines / chemical synthesis*
Benzoxazines / chemistry
Catalysis
Molecular Structure
Morpholines / chemical synthesis*
Morpholines / chemistry
Norbornanes / chemistry*
Oxazines / chemical synthesis*
Oxazines / chemistry
Palladium / chemistry*
Stereoisomerism

Substances

Benzoxazines
Morpholines
Norbornanes
Oxazines
Palladium
phenoxazine