Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition

Zachary A Kasun; Laina M Geary; Michael J Krische

doi:10.1039/c4cc03983a

Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition

Chem Commun (Camb). 2014 Jul 18;50(56):7545-7. doi: 10.1039/c4cc03983a.

Authors

Zachary A Kasun¹, Laina M Geary, Michael J Krische

Affiliation

¹ Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA. mkrische@mail.utexas.edu.

Abstract

A new method for the ring expansion of cyclic diols is described. Using improved conditions for the ruthenium(0) catalyzed cycloaddition of cyclic 1,2-diols with 1,3-dienes, fused [n.4.0] bicycles (n = 3-6) are formed, which upon exposure to iodosobenzene diacetate engage in oxidative cleavage to form the 9-12 membered rings .

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Cycloaddition Reaction / methods*
Hydrogenation
Ruthenium / chemistry*
Ruthenium / metabolism*

Substances

Ruthenium

Abstract

Publication types

MeSH terms

Substances

Grants and funding