Variable mechanism of nucleophilic substitution of P-stereogenic phosphoryl chloride with alkynyl metallic reagents
作者： Lan Yao , Li-Juan Liu , Zhong-Yuan Xu , Shao-Zhen Nie , Xiao-Qing Xiao
DOI: 10.1039/C5OB01871D
关键词:
摘要: The variable mechanism for substitution of P-stereogenic phosphoryl chloride with alkynyl metallic reagents, which depends on temperature, stoichiometry starting materials, and the structure nucleophilic reagent, is assumed as either SN2-like or Berry pseudorotation pentacoordinated phosphorus intermediates, affording inversion retention products, respectively. formation product can be controlled to occur predominantly afford (RP)-alkynylphosphinates.
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Neil Cockburn, Elham Karimi, William Tam, Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates. Journal of Organic Chemistry. ,vol. 74, pp. 5762- 5765 ,(2009) , 10.1021/JO9010206
Neil G. Andersen, Philip D. Ramsden, Daqing Che, Masood Parvez, Brian A. Keay, A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides. Journal of Organic Chemistry. ,vol. 66, pp. 7478- 7486 ,(2001) , 10.1021/JO015909U
Kamalraj V. Rajendran, Lorna Kennedy, Declan G. Gilheany, P‐Stereogenic Phosphorus Compounds: Effect of Aryl Substituents on the Oxidation of Arylmethylphenylphosphanes under Asymmetric Appel Conditions European Journal of Organic Chemistry. ,vol. 2010, pp. 5642- 5649 ,(2010) , 10.1002/EJOC.201000733
R. Stephen Berry, Correlation of Rates of Intramolecular Tunneling Processes, with Application to Some Group V Compounds Journal of Chemical Physics. ,vol. 32, pp. 933- 938 ,(1960) , 10.1063/1.1730820
Shiro Matsukawa, Satoshi Kojima, Kazumasa Kajiyama, Yohsuke Yamamoto, Kin-ya Akiba, Suyong Re, Shigeru Nagase, Characteristic reactions and properties of C-apical O-equatorial (O-cis) spirophosphoranes: effect of the sigma(P)(-)(O) orbital in the equatorial plane and isolation of a hexacoordinate oxaphosphetane as an intermediate of the Wittig type reaction of 10-P-5 phosphoranes. Journal of the American Chemical Society. ,vol. 124, pp. 13154- 13170 ,(2002) , 10.1021/JA026776C
Marcin Kalek, Tommy Johansson, Martina Jezowska, Jacek Stawinski, Palladium-Catalyzed Propargylic Substitution with Phosphorus Nucleophiles: Efficient, Stereoselective Synthesis of Allenylphosphonates and Related Compounds Organic Letters. ,vol. 12, pp. 4702- 4704 ,(2010) , 10.1021/OL102121J
Bradley O. Ashburn, Rich G. Carter, Lev N. Zakharov, Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a diels-alder approach Journal of the American Chemical Society. ,vol. 129, pp. 9109- 9116 ,(2007) , 10.1021/JA071163R
Li-Biao Han, Chang-Qiu Zhao, Shun-ya Onozawa, Midori Goto, Masato Tanaka, Retention of configuration on the oxidative addition of P-H bond to platinum (0) complexes: the first straightforward synthesis of enantiomerically pure P-chiral alkenylphosphinates via palladium-catalyzed stereospecific hydrophosphinylation of alkynes. Journal of the American Chemical Society. ,vol. 124, pp. 3842- 3843 ,(2002) , 10.1021/JA025816+
Ikenna Onyido, Krzysztof Swierczek, Jamie Purcell, Alvan C. Hengge, A concerted mechanism for the transfer of the thiophosphinoyl group from aryl dimethylphosphinothioate esters to oxyanionic nucleophiles in aqueous solution. Journal of the American Chemical Society. ,vol. 127, pp. 7703- 7711 ,(2005) , 10.1021/JA0501565
Jessica L. Menke, Eric V. Patterson, Quantum mechanical calculations on the reaction of ethoxide anion with O,S-dimethyl methylphosphonothiolate Journal of Molecular Structure: THEOCHEM. ,vol. 811, pp. 281- 291 ,(2007) , 10.1016/J.THEOCHEM.2006.11.033