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Thionoesters as 1,2‐Dipolarophiles for [4+2] Cycloaddition with Cyclobutanones
Author(s) -
Matsumoto Yohei,
Tsuji Taro,
Nakatake Daiki,
Yazaki Ryo,
Ohshima Takashi
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900156
Subject(s) - cycloaddition , chemistry , yield (engineering) , ketone , natural product , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
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 TiCl 4 . 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.