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Stereoselectivity in the Wittig‐Horner‐Emmons Synthesis of Vinylphosphonates by the Reaction of Acylphosphonates with Acyclic or Heterocyclic Phosphonoacetates
Author(s) -
Breuer Eli,
Moshe Ruth
Publication year - 1986
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198600008
Subject(s) - chemistry , phosphonate , stereoselectivity , wittig reaction , reagent , organic chemistry , medicinal chemistry , catalysis
A new synthetic approach to vinylphosphonates is presented. The reaction of diethyl benzoylphosphonate ( 1 ) with diethyl methoxycarbonyl‐methyl‐phosphonate ( 2 ) gives diethyl 2‐methoxycarbonyl‐l‐styrylphosphonate ( 3 ) as a mixture of geometrical isomers ( Z ‐3) and ( E ‐3) in the ratio of 83:17. In contrast, reaction of 1 with the heterocyclic phosphonate reagent, 2‐methoxycarbonyl‐methyl‐2‐oxo‐4,5‐dimethyl [1,3,2] dioxaphospholane ( 4 ) leads to a mixture of the isomers ( Z ‐3) and ( E ‐3) in the ratio of 20:80.