A stereoselective approach to the synthesis of (E)-alkoxydienylamines (2) is described, starting from alpha,beta-unsaturated acetals (1) and aryl imines, under superbasic conditions. These can be readily converted into alpha-arylglycine derivatives (3) by mild acidic hydrolysis or, in turn, cyclized under oxidative conditions in the presence of a Pd catalyst to 2,3,4,5-tetrasubstituted pyrroles (4).

LIC-KOR-Promoted Synthesis of Alkoxydienyl Amines: An Entry to 2,3,4,5-Tetrasubstituted Pyrroles

BLANGETTI, Marco;DEAGOSTINO, Annamaria;PRANDI, Cristina;TABASSO, Silvia;VENTURELLO, Paolo
2009

Abstract

A stereoselective approach to the synthesis of (E)-alkoxydienylamines (2) is described, starting from alpha,beta-unsaturated acetals (1) and aryl imines, under superbasic conditions. These can be readily converted into alpha-arylglycine derivatives (3) by mild acidic hydrolysis or, in turn, cyclized under oxidative conditions in the presence of a Pd catalyst to 2,3,4,5-tetrasubstituted pyrroles (4).
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http://pubs.acs.org/doi/abs/10.1021/ol9015018
Marco Blangetti; Annamaria Deagostino; Cristina Prandi; Silvia Tabasso; Paolo Venturello
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2318/61988
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