Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents

Chemistry : a European Journal
Sermadurai SelvakumarKeiji Maruoka

Abstract

Diastereoselective radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes is realized by the combination of a hypervalent iodine(III) reagent and UV-light irradiation. The reaction is initiated by the photolysis of hypervalent iodine(III) reagents under mild, metal-free conditions, and is the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The obtained optically active ketones are useful chiral synthons, as exemplified by the short formal synthesis of (-)-methyleneolactocin.

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Citations

Jun 24, 2017·Chemical Reviews·Hong YiAiwen Lei
Oct 24, 2017·Chemistry : a European Journal·Minh Duy VuXue-Wei Liu
Feb 7, 2020·Angewandte Chemie·Masaya NakajimaTetsuhiro Nemoto
Sep 21, 2017·Angewandte Chemie·Satobhisha MukherjeeFrank Glorius
Jul 30, 2019·ChemSusChem·Ioanna K SideriChristoforos G Kokotos
Dec 2, 2017·Chemistry : a European Journal·Giorgos N PapadopoulosChristoforos G Kokotos
Nov 20, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Akira MatsumotoKeiji Maruoka
Jun 12, 2021·Chemical Communications : Chem Comm·Yi-Lin LiuWen-Ting Wei

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