Stereoselective Dehydroxyboration of Allylic Alcohols to Access (E)-Allylboronates by a Combination of C-OH Cleavage and Boron Transfer under Iron Catalysis

Wei Su*, Ting-Ting Wang, Xia Tian, Jian-Rong Han, Xiao-Li Zhen, Shi-Ming Fan, Ya-Xin You, Yu-Kun Zhang, Rui-Xiao Qiao, Qiushi Cheng and Shouxin Liu*

*Hebei University of Science and Technology, Shijiazhuang 050022, China, Email: weisuhebust.edu.cn, chlsxhebust.edu.cn

W. Su, T.-T. Wang, X.-T. J.-R. Han, X.-L. Zhen, S.-M. Fan, Y.-X. You, Y.-K. Zhang, R.-X. Qiao, Q. Cheng, S. Liu, Org. Lett., 2021, 23, 9094-9099.

DOI: 10.1021/acs.orglett.1c03359

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Abstract

An iron-catalyzed direct S_N2' dehydroxyboration of allylic alcohols provides (E)-stereoselective allylboronates via a six-membered ring transition state. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation.

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proposed mechanism

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Key Words

allylboronates

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ID: J54-Y2021