Thionoesters as 1,2-Dipolarophiles for [4+2] Cycloaddition with Cyclobutanones

Yohei Matsumoto, Taro Tsuji, Daiki Nakatake, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)1071-1074
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume8
Issue number7
DOIs
Publication statusPublished - Jul 1 2019

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Cycloaddition
Carbon Monoxide
Biological Products
Ketones
Carbon
titanium tetrachloride

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Thionoesters as 1,2-Dipolarophiles for [4+2] Cycloaddition with Cyclobutanones. / Matsumoto, Yohei; Tsuji, Taro; Nakatake, Daiki; Yazaki, Ryo; Ohshima, Takashi.

In: Asian Journal of Organic Chemistry, Vol. 8, No. 7, 01.07.2019, p. 1071-1074.

Research output: Contribution to journalArticle

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