Stereocontrolled synthesis of complicated oxacyclic compounds via platinum-catalyzed [4 + 2]-cycloadditions and annulations of enynals with allylic alcohols

Yu-Chia Hsu; Chun-Ming Ting; Rai-Shung Liu

doi:10.1021/ja809560c

Stereocontrolled synthesis of complicated oxacyclic compounds via platinum-catalyzed [4 + 2]-cycloadditions and annulations of enynals with allylic alcohols

J Am Chem Soc. 2009 Feb 18;131(6):2090-1. doi: 10.1021/ja809560c.

Authors

Yu-Chia Hsu¹, Chun-Ming Ting, Rai-Shung Liu

Affiliation

¹ Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.

PMID: 19161254
DOI: 10.1021/ja809560c

Abstract

We report stereoselective synthesis of tricyclic ketals through Pt(II)-catalyzed [4 + 2]-cycloaddition of benzopyrilium/1-en-3-ol functionalities. For nonaromatic enynals, we obtained distinct tricyclic oxacyclic ketones due to occurrence of a new annulation reaction. This work reports the first example that [4 + 2]-cycloadducts are successfully intercepted from such functionalities in diversified approaches. The value of such cycloadditions and annulations are shown by their high diastereoselectivities and chemoselectivities.