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

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...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 21; pp. 11007 - 11016
Main Authors Oppedisano, Alberto, Prandi, Cristina, Venturello, Paolo, Deagostino, Annamaria, Goti, Giulio, Scarpi, Dina, Occhiato, Ernesto G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GOLD
CATALYSIS
NAZAROV REACTION
ACID
ENAMINONES
URETHANES
BETA-ENAMINOESTERS
CHEMISTRY
VERSATILE SYNTHESIS
DERIVATIVES
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4019914