2000
DOI: 10.1055/s-2000-6361
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Sequential Transformations of Phosphonates. One-Pot Synthesis of Ethoxycarbonyl Allyl Substituted Oxime Ethers

Abstract: Ketoxime anions 2, generated from the corresponding ketoximes 1 and sodium hydride, were reacted with a-ethoxycarbonyl vinylphosphonate 3 to give the phosphoryl-stabilized carbanions 4 which were further reacted with aldehydes affording ethoxycarbonyl allyl substituted oxime ethers in 73-91% yields.

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Cited by 15 publications
(4 citation statements)
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“…Shen and Jiang developed a convenient, one-pot synthesis of ethoxycarbonyl allyl substituted oxime ethers 313 by adding ketoxime anions 311 to ethyl 2-diethoxyphosphorylacrylate (76) (Scheme 61). 70 Olefination of aromatic aldehydes using anions 312 gave oxime ethers 313.…”
Section: Addition Of Heteronucleophiles Followed By Hwe Olefinationmentioning
confidence: 99%
“…Shen and Jiang developed a convenient, one-pot synthesis of ethoxycarbonyl allyl substituted oxime ethers 313 by adding ketoxime anions 311 to ethyl 2-diethoxyphosphorylacrylate (76) (Scheme 61). 70 Olefination of aromatic aldehydes using anions 312 gave oxime ethers 313.…”
Section: Addition Of Heteronucleophiles Followed By Hwe Olefinationmentioning
confidence: 99%
“…Vinylphosphonates are important synthetic intermediates and have been investigated as biologically active compounds . Vinylphosphonates have been used as intermediates in stereoselective synthesis of trisubstituted olefins , and in heterocycle synthesis . They have been also extensively used in polymer sciences as additives or flame-retardants .…”
Section: Introductionmentioning
confidence: 99%
“…4 A related example involves reaction of acetone oxime anion with α-ethoxycarbonyl vinylphosphonate resulting in a phosphonylstabilized carbanion 1, which can be utilized further (eq 3). 5 N OH CO …”
mentioning
confidence: 99%