首页|A one-pot diastereoselective synthesis of 1,3-diols and 1,3,5-triols via cascade reactions of arylalkynyl Grignard reagents with enol esters

A one-pot diastereoselective synthesis of 1,3-diols and 1,3,5-triols via cascade reactions of arylalkynyl Grignard reagents with enol esters

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An efficient cascade reaction has been developed to synthesize a series of 1,3-diols and 1,3,5-triols via reactions of arylalkynyl Grignard reagents with enol esters. The stereoselectivity of reactions and the molecular configurations of the products were confirmed by nuclear magnetic resonance, X-ray diffraction, and high-performance liquid chromatography analysis. A possible reaction mechanism was analyzed with the results indicating that it proceeded through a 1,2-addition/rearrangement and reverse O-acylation to produce the 1,3-diol and via C-acylation to form the 1,3,5-triol.

13-polyolsarylalkynyl Grignard reagentscascade reactionsenol estersreaction mechanism

Jiao, Yinchun、Zhao, Wenjing、Deng, Shuang、Tang, Zilong、Liu, Wanqiang、Wan, Yichao、Zhong, Fuqi

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Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China

2020

Journal of chemical research.

Journal of chemical research.

ISSN:1747-5198
年,卷(期):2020.44(5/6)
  • 44