Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 11884-11894Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01284
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Funding
- Japan Society of the Promotion of Science (JSPS KAKENHI) [17K05935, 20K05515]
- Grants-in-Aid for Scientific Research [20K05515, 17K05935] Funding Source: KAKEN
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The reaction proceeded via tandem Hosomi-Sakurai/Prins cyclization to produce polysubstituted tetrahydropyranones with high stereoselectivity. It is compatible with various aldehydes and ketones, and the optical purity of the starting material was well-retained in the final products.
beta-Silyl-gamma-ethylidene-gamma-butyrolactone upon one-pot treatment with aldehydes and ketones in the presence of Lewis acids underwent a tandem Hosomi-Sakurai/Prins cyclization to give polysubstituted tetrahydropyranones stereoselectively. Various aldehydes and ketones can be used in this reaction to produce the corresponding tetrahydropyranones. The optical purity of the starting gamma-butyrolactone was substantially retained in the resulting tetrahydropyranones.
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