Thermal [2 + 2]-Cycloaddition of Ketenes with Chiral Enol Ethers: Route to Densely Substituted Cyclobutanones

Pauline Rullière; Julien Grisel; Clément Poittevin; Pascale Cividino; Sébastien Carret; Jean-François Poisson

doi:10.1021/acs.orglett.6b01058

Thermal [2 + 2]-Cycloaddition of Ketenes with Chiral Enol Ethers: Route to Densely Substituted Cyclobutanones

Org Lett. 2016 Jun 17;18(12):2824-7. doi: 10.1021/acs.orglett.6b01058. Epub 2016 May 27.

Authors

Pauline Rullière^{1

2}, Julien Grisel^{1

2}, Clément Poittevin^{1

2}, Pascale Cividino^{1

2}, Sébastien Carret^{1

2}, Jean-François Poisson^{1

2}

Affiliations

¹ Univ. Grenoble Alpes, DCM , F-38000 Grenoble, France.
² CNRS, DCM , F-38000 Grenoble, France.

PMID: 27232587
DOI: 10.1021/acs.orglett.6b01058

Abstract

Access to chiral polysubstituted cyclobutanones by [2 + 2]-cycloaddition of ketenes with chiral acyclic enol ethers is reported. A wide variety of easily accessible di- and monosubstituted ketenes were found to react with a very high degree of stereoselectivity with chiral, Stericol derived, acyclic enol ethers. This combination of simple reagents provides straightforward entry to highly substituted enantioenriched cyclobutanones.

Publication types

Research Support, Non-U.S. Gov't