The gold(I)-catalyzed cyclization of N-Boc-protected 6-alkynyl-3,4-dihydro-2H-pyridines, prepared by the Sonogashira coupling of lactam-derived enol triflates or phosphates, provides vinylogous amides, which are useful intermediates in the synthesis of natural compounds. The Au(I)-catalyzed reaction is carried out with Ph3PAuOTf as a catalyst and proceeds via a 6-endo-dig cyclization to form a vinylgold species that after protodeauration generates a cyclic carbamate intermediate. This intermediate is in most cases not isolated, but the addition of a base to the reaction mixture rapidly and quantitatively delivers the target vinylogous amide. The first synthesis of a natural compound from Sonneratia hainanensis has been accomplished by this approach.

Synthesis of Vinylogous Amides by Gold(I)-Catalyzed Cyclization of N-Boc-Protected 6-Alkynyl-3,4-dihydro-2H-pyridines

PRANDI, Cristina;VENTURELLO, Paolo;DEAGOSTINO, Annamaria;
2013-01-01

Abstract

The gold(I)-catalyzed cyclization of N-Boc-protected 6-alkynyl-3,4-dihydro-2H-pyridines, prepared by the Sonogashira coupling of lactam-derived enol triflates or phosphates, provides vinylogous amides, which are useful intermediates in the synthesis of natural compounds. The Au(I)-catalyzed reaction is carried out with Ph3PAuOTf as a catalyst and proceeds via a 6-endo-dig cyclization to form a vinylgold species that after protodeauration generates a cyclic carbamate intermediate. This intermediate is in most cases not isolated, but the addition of a base to the reaction mixture rapidly and quantitatively delivers the target vinylogous amide. The first synthesis of a natural compound from Sonneratia hainanensis has been accomplished by this approach.
2013
78
21
11007
11016
http://pubs.acs.org/doi/abs/10.1021/jo4019914?prevSearch=[Contrib:+prandi]&searchHistoryKey=
Alberto Oppedisano; Cristina Prandi; Paolo Venturello; Umit Calisir; Annamaria Deagostino; Giulio Goti; Dina Scarpi; Ernesto G. Occhiato
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/140035
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