Synthesis 2015; 47(01): 22-33
DOI: 10.1055/s-0034-1378918
short review
© Georg Thieme Verlag Stuttgart · New York

(3+2)-Cycloaddition Reactions of Oxyallyl Cations

Hui Li, Jimmy Wu*
  • Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA   Fax: +1(603)6463946   Email: jimmy.wu@dartmouth.edu
Further Information

Publication History

Received: 30 July 2014

Accepted after revision: 09 October 2014

Publication Date:
10 November 2014 (eFirst)

Abstract

The (3+2)-cycloaddition reaction involving oxyallyl cations has proven to be a versatile and efficient approach for the construction of five-membered carbo- and heterocycles, which are prevalent frameworks in natural products and pharmaceuticals. The following article will provide a brief summary of recent disclosures on this process featuring chemo-, regio- and diastereoselective oxyallyl cycloadditions with both electron-rich and electron-deficient 2π partners.

1 Introduction

2 Heteroatom-Substituted Oxyallyl Cations

3 Oxyallyl Cations Derived from Substituted Ketones

4 Oxyallyl Cations Intercepted from Nazarov Cyclization

5 1-Alkylidene-2-oxyallyl Cations

6 Summary and Outlook