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

Masahiro Inoue Department of Chemistry, School of Science and Engineering, Waseda University, Ohkubo, Shinjuku-ku, Tokyo, Japan

Shinji Motomatsu Department of Chemistry, School of Science and Engineering, Waseda University, Ohkubo, Shinjuku-ku, Tokyo, Japan

Masahisa Nakada Department of Chemistry, School of Science and Engineering, Waseda University, Ohkubo, Shinjuku-ku, Tokyo, JapanCorrespondence[email protected]

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.

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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 ).

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

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

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