Journal
ORGANIC LETTERS
Volume 24, Issue 13, Pages 2579-2584Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00942
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Funding
- National Natural Science Foundation of China [22071186, 22071187]
- Natural Science Foundation of Hubei Province [2020CFA036, 2021CFA069]
- Natural Science Foundation of Jiangsu Province [BK20190213]
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In this study, an iridium-catalyzed cascade allylation/macrolactonization reaction was developed, which efficiently synthesizes chiral macrodiolides with excellent diastereoselectivities and enantioselectivities. This method is characterized by readily available substrates, high stereoselective control, and efficient synthetic steps.
Iridium-catalyzed cascade allylation/macrolactonization between vinylethylene carbonate (VEC) and isatoic anhydride derivatives was successfully developed, readily generating a wide range of C-2-symmetric chiral macrodiolides bearing 14-membered rings in moderate to good yields with excellent diastereoselectivities and enantioselectivities (generally 99% ee). Control experiments revealed that racemic VEC as the precursor of electrophilic iridium-pi-allyl species underwent kinetic resolution process. This expedient protocol features easily available substrates, excellent stereoselective control, and high step economy.
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