TY - JOUR
T1 - Thionoesters as 1,2-Dipolarophiles for [4+2] Cycloaddition with Cyclobutanones
AU - Matsumoto, Yohei
AU - Tsuji, Taro
AU - Nakatake, Daiki
AU - Yazaki, Ryo
AU - Ohshima, Takashi
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Number JP15H05846 in Middle Molecular Strategy, JP18H04263in Precisely Designed Catalysts with Customized Scaffolding, Grant-in-Aid for Scientific Research (B) (#17H03972), Grant-in-Aid for Scientific Research (C) (#16 K08166) and Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP17am0101091. D.N. thanks JSPS for a predoctoral fellowship.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/7
Y1 - 2019/7
N2 - 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.
AB - 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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U2 - 10.1002/ajoc.201900156
DO - 10.1002/ajoc.201900156
M3 - Article
AN - SCOPUS:85063984224
SN - 2193-5807
VL - 8
SP - 1071
EP - 1074
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 7
ER -