Issue 24, 2022

Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine

Abstract

Despite the rapid growth of enantioselective halolactonization reactions in recent years, most are effective only when forming smaller (6,5,4-membered) rings. Seven-membered ε-lactones, are rarely formed with high selectivity, and never without conformational bias. We describe the first highly enantioselective 7-exo-trig iodolactonizations of conformationally unbiased ε-unsaturated carboxylic acids, effected by an unusual combination of a bifunctional BAM catalyst, I2, and I(III) reagent (PhI(OAc)2:PIDA).

Graphical abstract: Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Mar 2022
Accepted
25 May 2022
First published
08 Jun 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 7318-7324

Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine

J. L. Payne, Z. Deng, A. L. Flach and J. N. Johnston, Chem. Sci., 2022, 13, 7318 DOI: 10.1039/D2SC01587K

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