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

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

研究成果: Contribution to journalArticle

抜粋

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.

元の言語英語
ページ(範囲)1071-1074
ページ数4
ジャーナルAsian Journal of Organic Chemistry
8
発行部数7
DOI
出版物ステータス出版済み - 7 1 2019

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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