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Synthesis 2000; 2000(11): 1535-1538
DOI: 10.1055/s-2000-7596
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Stereocontrolled Synthesis of Fluorinated (E)- or (Z)-Allylic Phosphonates

Yanchang Shen* , Yuming Zhang, Zenghong Zhang
  • *Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Academia Sinica, 354 Fenglin Lu, Shanghai 20032, China; E-mail: shenyc@pub.sioc.ac.cn
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Publication Date:
31 December 2000 (online)

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Treatment of (dicarbonylmethylene)triphenylphosphoranes 1 with [(diethoxylphosphinoyl)methyl]lithium (2a) gave 3a, followed by protonation and elimination of triphenylphosphine oxide, to afford the Z-isomer exclusively (4b, 4e, 4f, 4g); while [(dialkoxyphosphinoyl)alkyl]lithium (2b) reacted with 1 under the same conditions, to give the E-isomers exclusively (4a, 4c, 4d) or predominantly (4h, 4i, 4j). Thus this methodology provides a stereocontrolled synthesis of the title compounds.

stereocontrolled synthesis - (E)- or (Z)-allylic phosphonates - fluorinated allylic phosphonates - fluorine - phosphorus