Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives

Abstract

Abstract: The tandem asymmetric Michael addition/internal Michalis Arbazov reaction of compound 1 with nucleophilic trialkylphosphites has been investigated. The asymmetric reaction afforded optically pure-5-(1S) bornyloxy-4-dialkyloxy phosphonyl-3-halo-2(5H) furanones 3a_3d at a mild condition in 69%-95% yield with d.e.≥98%. The chemical structure and configuration of the chiral compounds 3a₃d were identified on the basis of their elemental analytical data and spectroscopic data, such as [α]_D²⁰ , UV, IR, ¹H NMR, ¹³C NMR, MSand Xray crystallography.

Key words: New chiral phosphonate reagent, Tandem asymmetric Michael addition/Intromolecular Michalis Arbazov rearangement reaction, Crystal structure, 5 (1 S ) Bornyloxy₄ dialkyloxyphosphonyl₃ halo₂(5H) furanone

CLC Number:

O621

TrendMD:

LI Xue-Qiang, CHEN Qinq-Hua . Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives[J]. Chem. J. Chinese Universities, 2001, 22(10): 1677.

References

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