Highly Z-Selective Synthesis of Highly Substituted 1,3-Oxathiolane-2-imines via TfOH-Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Isothiocyanates

Zhan，Feng1,2; Wang，Zhe1,2; Wu，Guan Zheng1,2; Shi，Zhichao1,2; Zhang，Xun1,2; Zuo，Qinglu1,2; Lin，Jin Shun1,2; Jiang，Yuyang1,2,3,4,5

2021-04-08

10.1002/slct.202100637

ChemistrySelect   影响因子和分区

2365-6549

TfOH-catalyzed [3+2] cycloaddition of donor-acceptor oxiranes with isothiocyanates via chemoselective C−O bond breakage of D−A oxiranes was developed under metal- and additive-free conditions. This method providing a facile access to a diverse range of highly substituted 1,3-oxathiolane-2-imines in good to excellent yields and with high Z-selectivity and excellent functional group tolerance. In addition, the established protocol can be easily scaled up to gram level in excellent yield. Furthermore, transformation of cycloadduct into 1,3-oxathiolane-2-one by acid hydrolysis of the imino group is easily achieved in moderate yield.

1,3-oxathiolane-2-imines D−A oxiranes high Z-selectivity isothiocyanates TfOH-catalyzed

SCI

英语

其他

WOS:000656857900011

2-s2.0-85107551673

Scopus

1.Department of Chemistry,Tsinghua University,Beijing,100084,China
2.The State Key Laboratory of Chemical Oncogenomics,Key Laboratory of Chemical Biology,Tsinghua Shenzhen International Graduate School,Tsinghua University,Shenzhen,518055,China
3.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
4.Shenzhen Bay Laboratory,Shenzhen,518055,China
5.School of Pharmaceutical Sciences,Tsinghua University,Beijing,100084,China

Zhan，Feng,Wang，Zhe,Wu，Guan Zheng,et al. Highly Z-Selective Synthesis of Highly Substituted 1,3-Oxathiolane-2-imines via TfOH-Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Isothiocyanates[J]. ChemistrySelect,2021,6(13):3151-3154.

Zhan，Feng.,Wang，Zhe.,Wu，Guan Zheng.,Shi，Zhichao.,Zhang，Xun.,...&Jiang，Yuyang.(2021).Highly Z-Selective Synthesis of Highly Substituted 1,3-Oxathiolane-2-imines via TfOH-Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Isothiocyanates.ChemistrySelect,6(13),3151-3154.

Zhan，Feng,et al."Highly Z-Selective Synthesis of Highly Substituted 1,3-Oxathiolane-2-imines via TfOH-Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Isothiocyanates".ChemistrySelect 6.13(2021):3151-3154.