Gold(I)-catalyzed three-component additions of 2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols: an efficient access to 3-oxabicyclo[3.1.0]hexanes

Guo-Qiang Tian; Min Shi

doi:10.1021/ol702341a

Gold(I)-catalyzed three-component additions of 2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols: an efficient access to 3-oxabicyclo[3.1.0]hexanes

Org Lett. 2007 Nov 8;9(23):4917-20. doi: 10.1021/ol702341a. Epub 2007 Oct 18.

Authors

Guo-Qiang Tian¹, Min Shi

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China.

PMID: 17944482
DOI: 10.1021/ol702341a

Abstract

Catalyzed by gold(I), (E)- and (Z)-2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols underwent three-component addition reactions to produce 3-oxabicyclo[3.1.0]hexanes in high yields and moderate diastereoselectivities under mild conditions. A plausible mechanism based on an intermolecular tandem hydroalkoxylation/Prins-type reaction pathway has been proposed.