Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 7, Pages 1071-1074Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201900156
Keywords
thionoester; dipolarophile; cycloaddition; tetrahydrothiopyran; diastereoselective
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Funding
- JSPS KAKENHI [JP15H05846, JP18H04263]
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED [JP17am0101091]
- JSPS
- [17H03972]
- [16 K08166]
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The utility of thionoester as a 1,2-dipolarophile for [4+2] cycloaddition with cyclobutanones is described. The [4+2] cycloaddition reaction provided tetrahydrothiopyran, which is found in biologically active natural products, in high yield with high diastereoselectivity by using readily available TiCl4. This synthetic method was applicable to a wide range of thionoesters and cyclobutanones. The ketone and S,O-ketal functionalities of the product could be reduced with excellent diastereoselectivity. Furthermore, the C-O bond was transformed into a C-C bond, affording contiguous tetrasubstituted carbon centers.
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