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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 12: 4261 - 4267

DOI: https://doi.org/10.6023/cjoc202306012

ARTICLES

Lanthanum Silylamide-Catalyzed Synthesis of Enol Phosphates

  • Kang Pan ,
  • Fan Xu
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  • College of Chemistry, Chemical Engineering and Material Science, Soochow University, Suzhou 215123
*

Received date: 2023-06-15

  Revised date: 2023-07-13

  Online published: 2023-07-27

Supported by

Natural Science Foundation of the Jiangsu Higher Education Institutions(18KJA150007)

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Abstract

Enol phosphate has important applicative value in many fields. The development of a catalytic and selective method for the synthesis of enol phosphate is of great significance. The reaction of 4-oxo-4-arylbut-2-enoate and diethyl phosphite catalyzed by lanthanum silylamide [(Me3Si)2N]3La(μ-Cl)Li(THF)3 is developed, which provides a series of enol phosphates in cis-configuration. Research on the mechanism indicates that the reaction undergoes a relatively rare [1,4]-phospha-Brook rearrangement. The reaction has advantages of ready availability of catalyst and high selectivity for alkenyl configuration, providing an efficient method for the synthesis of enol phosphates.

Key words： enol phosphate; lanthanide silylamide; catalysis; phospha-Brook rearrangement; stereoselectivity

Cite this article

Kang Pan , Fan Xu . Lanthanum Silylamide-Catalyzed Synthesis of Enol Phosphates[J]. Chinese Journal of Organic Chemistry, 2023 , 43(12) : 4261 -4267 . DOI: 10.6023/cjoc202306012

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