Enantioselective synthesis of chiral sulfones by Ir-catalyzed asymmetric hydrogenation: a facile approach to the preparation of chiral allylic and homoallylic compounds

Taigang Zhou; Byron Peters; Matías F Maldonado; Thavendran Govender; Pher G Andersson

doi:10.1021/ja306731u

Enantioselective synthesis of chiral sulfones by Ir-catalyzed asymmetric hydrogenation: a facile approach to the preparation of chiral allylic and homoallylic compounds

J Am Chem Soc. 2012 Aug 22;134(33):13592-5. doi: 10.1021/ja306731u. Epub 2012 Aug 7.

Authors

Taigang Zhou¹, Byron Peters, Matías F Maldonado, Thavendran Govender, Pher G Andersson

Affiliation

¹ Department of Chemistry-BMC, Uppsala University, Box 576, S-75123 Uppsala, Sweden.

PMID: 22835144
DOI: 10.1021/ja306731u

Abstract

A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).

Publication types

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

MeSH terms

Allyl Compounds / chemical synthesis*
Allyl Compounds / chemistry
Catalysis
Hydrogenation
Iridium / chemistry*
Stereoisomerism
Sulfones / chemical synthesis*
Sulfones / chemistry

Substances

Allyl Compounds
Sulfones
Iridium