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Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates

Peter B. Rapp, Koichi Murai, Naoko Ichiishi, David K. Leahy* and Scott J. Miller*

*Takeda Pharmaceuticals Int. Co., Cambridge, Massachusetts 02139; Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States, Email: david.leahytakeda.com, scott.milleryale.edu

P. B. Rapp, K. Murai, N. Ichiishi, D. K. Leahy, S. J. Miller, Org. Lett., 2020, 22, 168-174.

DOI: 10.1021/acs.orglett.9b04119


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Abstract

N-Methylimidazole catalyzes alcohol sulfamoylation using electron-deficient aryl sulfamates as activated group transfer reagents under mild conditions. The reaction provides intrinsic selectivity for 1 over 2 alcohols. The requisite aryl sulfamate donors are stable crystalline solids that can be readily prepared on a large scale.

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Key Words

sulfamoylation


ID: J54-Y2020