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Chiral diaryliodonium phosphate enables light driven diastereoselective α- C(sp3)-H acetalization

Ye, Baihua and Zhao, Jie and Zhao, Ke and Mckenna, Jeffrey and Toste, F Dean (2018) Chiral diaryliodonium phosphate enables light driven diastereoselective α- C(sp3)-H acetalization. Journal of the American Chemical Society JACS., 140.

Abstract

C(sp3)-H bond functionalization has emerged as a robust tool enabling rapid construction of molecular complexity from simple building blocks: the development of asymmetric versions of this reaction creates a powerful methodology to access enantiopure sp3-rich materials. Although numerous metal-mediated versions have been developed which are reliant upon a proximal directing group, HAT-mediated versions are at a boundary of reactivity that means the development of these reactions remain enormously challenging. Herein, we report a new asymmetric functionalization of C(sp3)-H bonds through the introduction of a photochemically active diaryliodonium salt into our anionic phase-transfer catalysis methodology. The synthetic strategy outlined herein provides a novel pathway to control the regio- and stereo-chemical outcome in the α C-H acetalization of cyclic ethers. This methodology has both a wide scope and the ability to control the configuration at the stereogenic exocyclic acetal carbon.

Item Type: Article
Date Deposited: 08 Aug 2018 00:45
Last Modified: 08 Aug 2018 00:45
URI: https://oak.novartis.com/id/eprint/35973

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