Base-Induced Enantioselective Synthesis of Sulfinyl Dihydropyrans

2-Sulfinyl dienols undergo an efficient base-promoted cyclization to produce sulfinyl dihydropyrans with creation of two asymmetric centers. The configurational stability of the allylic sulfoxide in most cases is noteworthy. Simple manipulations lead to a variety of functionalized tetrahydropyrans.

keywords:

• Allylic sulfoxides;
• asymmetric synthesis;
• dihydropyrans;
• tetrahydropyrans

Acknowledgments

This research was supported by DGICYT (BQU2001-0582 and BQU2003-02921) and CAM (08.5/0028/2003 2). We thank Janssen-Cilag for generous additional support. We thank MEC for a doctoral fellowship to M. T.