(Poly)cationic λ3 -Iodane Mediated Oxidative Ring Expansion of Secondary Alcohols

European Journal of Organic Chemistry
Jennifer C WaltersSarah E Wengryniuk

Abstract

Herein, we report a simplified approach to the synthesis of medium-ring ethers through the electrophilic activation of secondary alcohols with (poly)cationic λ3-iodanes (N-HVI). Excellent levels of selectivity are achieved for C-O bond migration over established α-elimination pathways, enabled by the unique reactivity of a novel 2-OMe-pyridine-ligated N-HVI. The resulting HFIP-acetals are readily derivatized with a range of nucleophiles, providing a versatile functional handle for subsequent manipulations. The utility of this methodology for late-stage natural product derivatization was also demonstrated, providing a new tool for diversity-oriented synthesis and complexity-to-diversity (CTD) efforts. Preliminary mechanistic investigations reveal a strong effect of alcohol conformation on reactive pathway, thus providing a predictive power in the application of this approach to complex molecule synthesis.

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Citations

Sep 25, 2018·Organic & Biomolecular Chemistry·Harsimran K MinhasMartyna Urbonaite
Jul 12, 2019·Angewandte Chemie·Anastassia Matviitsuk, Scott E Denmark
May 27, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Sathsara EgalahewaJason L Dutton
Nov 4, 2020·Chemical Communications : Chem Comm·Beibei ZhangYunfei Du
Dec 10, 2020·Organic & Biomolecular Chemistry·Shuang YangZhenhua Ding
Apr 20, 2021·The Journal of Organic Chemistry·Xiao XiaoSarah E Wengryniuk
Jul 8, 2021·Chemical Communications : Chem Comm·Andreas BoelkeBoris J Nachtsheim
Apr 19, 2019·Organic Letters·Wataru YamakoshiKenichi Murai
Dec 17, 2019·Journal of the American Chemical Society·Felipe Cesar Sousa E SilvaSarah E Wengryniuk
Jul 17, 2019·Organic Letters·Myriam MikhaelSarah E Wengryniuk
Oct 22, 2021·The Journal of Organic Chemistry·Travis MenardScott E Denmark
Nov 3, 2021·Chemical Communications : Chem Comm·Aseel BakroJason L Dutton

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