Highly Diastereoselective Preparation of Cyclic Sulfates from Allyl and Homoallyl Alcohols via One-Pot Halocyclosulfations

Abstract

Diastereoselective electrophilic heteroatom cyclizations of the monosulfates of homoallyl and allyl alcohols are described. This cyclization tends to afford thermodynamically favored products, and high 1,3-asymmetric induction is observed in the case of homoallyl alcohols.

Keywords:

• Allyl alcohol
• Asymmetric induction
• Cyclic sulfate
• Halocyclosulfation
• Homoallyl alcohol

Acknowledgments

This work was supported in part by Waseda University Grant for Special Research Projects (Individual Research). We thank Dr. Motoo Shiro of Rigaku X-Ray Research Laboratory for the X-ray crystal structure determination of 2a( syn ).