Title

The intramolecular allenolate rauhut-currier reaction

Document Type

Article

Publication Title

Journal of Organic Chemistry

Publication Date

9-7-2012

Abstract

An intramolecular Rauhut-Currier reaction utilizing alkynoates as the initial conjugate acceptor affords densely functionalized 5- and 6-membered rings from ynoate-enoate, ynoate-enenitrile, and alkynyl sulfone-enenitrile substrates. Trialkylphosphines catalyze the reaction, and TMSCN serves as a pronucelophile to effect turnover of the catalyst and the formation of a second C-C bond. Because of the highly electrophilic alkyne acceptor, this reaction yields products that cannot be easily accessed from the traditional Rauhut-Currier reaction. © 2012 American Chemical Society.

Volume

77

Issue

17

First Page

7768

Last Page

7774

DOI

10.1021/jo3015769

ISSN

00223263

E-ISSN

15206904

PubMed ID

22866944

Link to Full Text

Share

COinS