We studied the reactions of vinyl phosphates and vinyl phosphordiamidates containing an ester functional group with organometallic reagents. We found that the functionalized vinyl phosphates were smoothly converted into tri- and tetrasubstituted buta-1,3-dienes via the reaction with aryllithium reagents. Moreover, the vinyl phosphordiamidates were converted into α,β-unsaturated ketones using Grignard reagents. Based on the performed experiments, we proposed a reaction mechanism, which was confirmed by means of the isolation of key intermediates.

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

Laboratory of NMR Spectroscopy University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

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Adrio J. Carretero J. C. ChemCatChem. 2010;2:1384–1386. doi: 10.1002/cctc.201000237. DOI

Heravi M. M. Hajiabbasi P. Monatsh. Chem. 2012;143:1575–1592. doi: 10.1007/s00706-012-0838-x. DOI

Heravi M. M. Zadsirjan V. Hajiabbasi P. Hamidi H. Monatsh. Chem. 2019;150:535–591. doi: 10.1007/s00706-019-2364-6. DOI

Ambre R. Yang H. Chen W.-C. Yap G. P. A. Jurca T. Ong T.-G. Eur. J. Inorg. Chem. 2019:3511–3517. doi: 10.1002/ejic.201900692. DOI

Fan F. Tang J. Luo M. Zeng X. J. Org. Chem. 2018;83:13549–13559. doi: 10.1021/acs.joc.8b02104. PubMed DOI

Chen P.-P. Lucas E. L. Greene M. A. Zhang S.-Q. Tollefson E. J. Erickson L. W. Taylor B. L. H. Jarvo E. R. Hong X. J. Am. Chem. Soc. 2019;141:5835–5855. doi: 10.1021/jacs.9b00097. PubMed DOI PMC

Ghorai D. Loup J. Zanoni G. Ackermann L. Synlett. 2019;30:429–432. doi: 10.1055/s-0037-1611663. DOI

Piontek A. Ochędzan-Siodłak W. Bisz E. Szostak M. Adv. Synth. Catal. 2019;361:2329–2336. doi: 10.1002/adsc.201801586. DOI

Sato Y. Ashida Y. Yoshitake D. Hoshino M. Takemoto T. Tanabe Y. Synthesis. 2018;50:4659–4667. doi: 10.1055/s-0037-1610652. DOI

Quesnelle C. A. Snieckus V. Synthesis. 2018;50:4395–4412. doi: 10.1055/s-0037-1611053. DOI

Manikandan R. Jeganmohan M. Org. Biomol. Chem. 2015;13:10420–10436. doi: 10.1039/C5OB01472G. PubMed DOI

Negishi E.-i. Wang G. Rao H. Xu Z. J. Org. Chem. 2010;75:3151–3182. doi: 10.1021/jo1003218. PubMed DOI PMC

Siau W.-Y., Zhang Y. and Zhao Y., in Stereoselective Alkene Synthesis, ed. J. Wang, Springer Berlin Heidelberg, Berlin, Heidelberg, 2012, pp. 33–58, 10.1007/128_2012_315 DOI

Drouin M. Hamel J.-D. Paquin J.-F. Synthesis. 2018;50:881–955. doi: 10.1055/s-0036-1591867. DOI

Maraswami M. Loh T.-P. Synthesis. 2019;51:1049–1062. doi: 10.1055/s-0037-1611649. DOI

Polák P. Váňová H. Dvořák D. Tobrman T. Tetrahedron Lett. 2016;57:3684–3693. doi: 10.1016/j.tetlet.2016.07.030. DOI

Cahiez G. Habiak V. Gager O. Org. Lett. 2008;10:2389–2392. doi: 10.1021/ol800816f. PubMed DOI

Cahiez G. Avedissian H. Synthesis. 1998:1199–1205. doi: 10.1055/s-1998-2135. DOI

Cahiez G. Gager O. Habiak V. Synthesis. 2008:2636–2644. doi: 10.1055/s-2008-1067194. DOI

Fiorito D. Folliet S. Liu Y. Mazet C. ACS Catal. 2018;8:1392–1398. doi: 10.1021/acscatal.7b04030. DOI

Karlström A. S. E. Itami K. Bäckvall J.-E. J. Org. Chem. 1999;64:1745–1749. doi: 10.1021/jo982060h. PubMed DOI

Sahlberg C. Quader A. Claesson A. Tetrahedron Lett. 1983;24:5137–5138. doi: 10.1016/S0040-4039(00)94062-0. DOI

Gauthier D. Beckendorf S. Gøgsig T. M. Lindhardt A. T. Skrydstrup T. J. Org. Chem. 2009;74:3536–3539. doi: 10.1021/jo900098a. PubMed DOI

You W. Li Y. Brown M. K. Org. Lett. 2013;15:1610–1613. doi: 10.1021/ol400392r. PubMed DOI

Miller J. A. Tetrahedron Lett. 2002;43:7111–7114. doi: 10.1016/S0040-4039(02)01600-3. DOI

Knochel P. Dohle W. Gommermann N. Kneisel F. F. Kopp F. Korn T. Sapountzis I. Vu V. A. Angew. Chem., Int. Ed. 2003;42:4302–4320. doi: 10.1002/anie.200300579. PubMed DOI

Ila H. Baron O. Wagner A. J. Knochel P. Chem. Commun. 2006:583–593. doi: 10.1039/B510866G. PubMed DOI

Li-Yuan Bao R. Zhao R. Shi L. Chem. Commun. 2015;51:6884–6900. doi: 10.1039/C4CC10194D. PubMed DOI

Knappke C. E. I. Jacobi von Wangelin A. Chem. Soc. Rev. 2011;40:4948–4962. doi: 10.1039/C1CS15137A. PubMed DOI

Silveira C. C. Guerra R. B. Comasseto J. V. Tetrahedron Lett. 2007;48:5121–5124. doi: 10.1016/j.tetlet.2007.05.074. DOI

Barrientos-Astigarraga R. E. Castelani P. Sumida C. Y. Zukerman-Schpector J. Comasseto J. V. Tetrahedron. 2002;58:1051–1059. doi: 10.1016/S0040-4020(01)01204-2. DOI

Sum F.-W. Weiler L. Can. J. Chem. 1979;57:1431–1441. doi: 10.1139/v79-234. DOI

Yoshitaka O. J. Tomofumi T. Teruaki M. Chem. Lett. 2003;32:994–995. doi: 10.1246/cl.2003.994. DOI

Bach T. Höfer F. J. Org. Chem. 2001;66:3427–3434. doi: 10.1021/jo001740t. PubMed DOI

Brown R. C. D. Bataille C. J. Hughes R. M. Kenney A. Luker T. J. J. Org. Chem. 2002;67:8079–8085. doi: 10.1021/jo026295b. PubMed DOI

Thulasiram H. V. Phan R. M. Rivera S. B. Poulter C. D. J. Org. Chem. 2006;71:1739–1741. doi: 10.1021/jo052384n. PubMed DOI PMC

Piva O. J. Org. Chem. 1995;60:7879–7883. doi: 10.1021/jo00129a030. DOI

Reber K. P. Xu J. Guerrero C. A. J. Org. Chem. 2015;80:2397–2406. doi: 10.1021/jo502602u. PubMed DOI

Nawrat C. C. Moody C. J. Org. Lett. 2012;14:1484–1487. doi: 10.1021/ol300221e. PubMed DOI

Ishigami K. Yamada S. Watanabe H. Tetrahedron Lett. 2015;56:5816–5819. doi: 10.1016/j.tetlet.2015.09.011. DOI

Hashimoto S.-i. Ban M. Yanagiya Y. Sakata S. Ikegami S. Tetrahedron Lett. 1991;32:4027–4030. doi: 10.1016/0040-4039(91)80618-G. DOI

Das D. Kant R. Chakraborty T. K. Org. Lett. 2014;16:2618–2621. doi: 10.1021/ol500768w. PubMed DOI

Cheng H. M. Tian W. Peixoto P. A. Dhudshia B. Chen D. Y.-K. Angew. Chem., Int. Ed. 2011;50:4165–4168. doi: 10.1002/anie.201100926. PubMed DOI

Hayashi N. Yamamoto K. Minowa N. Mitomi M. Nakada M. Org. Biomol. Chem. 2010;8:1821–1825. doi: 10.1039/B924096A. PubMed DOI

Hayashi N. Nakada M. Tetrahedron Lett. 2009;50:232–235. doi: 10.1016/j.tetlet.2008.10.138. DOI

Gampe C. M. Tsukamoto H. Wang T.-S. A. Walker S. Kahne D. Tetrahedron. 2011;67:9771–9778. doi: 10.1016/j.tet.2011.09.114. PubMed DOI PMC

Polla M. Frejd T. Tetrahedron. 1993;49:2701–2710. doi: 10.1016/S0040-4020(01)86347-X. DOI

Pettersson L. Magnusson G. Frejd T. Pakkanen T. A. Négrel J. C. Chanon M. Striley C. Weidlein J. Nasiri A. Okada Y. Acta Chem. Scand. 1993;47:196–207. doi: 10.3891/acta.chem.scand.47-0196. DOI

Aggarwal V. K. Bethel P. A. Giles R. Chem. Commun. 1999:325–326. doi: 10.1039/A808644C. DOI

Polák P. Tobrman T. Eur. J. Org. Chem. 2019:957–968. doi: 10.1002/ejoc.201801522. DOI

Polák P. Tobrman T. Org. Biomol. Chem. 2017;15:6233–6241. doi: 10.1039/C7OB01127J. PubMed DOI

Kotek V. Polák P. Dvořáková H. Tobrman T. Eur. J. Org. Chem. 2016:5037–5044. doi: 10.1002/ejoc.201600959. DOI

Kotek V. Dvořáková H. Tobrman T. Org. Lett. 2015;17:608–611. doi: 10.1021/ol503624v. PubMed DOI

Barluenga J. Tomás-Gamasa M. Aznar F. Valdés C. Adv. Synth. Catal. 2010;352:3235–3240. doi: 10.1002/adsc.201000700. DOI

Zou Y. Qin L. Ren X. Lu Y. Li Y. Zhou J. Chem.–Eur. J. 2013;19:3504–3511. doi: 10.1002/chem.201203646. PubMed DOI

Wang R. Zhang S. RSC Adv. 2014;4:39497–39507. doi: 10.1039/C4RA06256F. DOI

Hossain M. Das U. Dimmock J. R. Eur. J. Med. Chem. 2019;183:111687. doi: 10.1016/j.ejmech.2019.111687. PubMed DOI

Boruah R. C. Nongthombam G. S. Heterocycles. 2019;98:19–62. doi: 10.3987/REV-18-898. DOI

Meyer C. C. Ortiz E. Krische M. J. Chem. Rev. 2020;120:3721–3748. doi: 10.1021/acs.chemrev.0c00053. PubMed DOI PMC

Lam J. Szkop K. M. Mosaferi E. Stephan D. W. Chem. Soc. Rev. 2019;48:3592–3612. doi: 10.1039/C8CS00277K. PubMed DOI

Douchez A. Geranurimi A. Lubell W. D. Acc. Chem. Res. 2018;51:2574–2588. doi: 10.1021/acs.accounts.8b00388. PubMed DOI

Zhang S. Neumann H. Beller M. Chem. Soc. Rev. 2020;49:3187–3210. doi: 10.1039/C9CS00615J. PubMed DOI

Jiang C. Lu H. Xu W.-H. Wu J. Yu T.-Y. Xu P.-F. Wei H. ACS Catal. 2020;10:1947–1953. doi: 10.1021/acscatal.9b04112. DOI

Nájera C. Sydnes L. K. Yus M. Chem. Rev. 2019;119:11110–11244. doi: 10.1021/acs.chemrev.9b00277. PubMed DOI

Pan F.-F. Guo P. Li C.-L. Su P. Shu X.-Z. Org. Lett. 2019;21:3701–3705. doi: 10.1021/acs.orglett.9b01164. PubMed DOI

An Y.-L. Li K. Shen Y. Hong Z. Chen L. Hu Y. Zhou L. Wang D. Shi X. Liu S. Su W. Cui W. Kuai L. Yang H. Peng X. Org. Lett. 2020;22:3931–3935. doi: 10.1021/acs.orglett.0c01215. PubMed DOI

Rhee J. U. Krische M. J. Org. Lett. 2005;7:2493–2495. doi: 10.1021/ol050838x. PubMed DOI

Kreutzkamp N. Pluhatsch J. Schindler H. Arch. Pharm. 1960;293:900–907. doi: 10.1002/ardp.19602931005. PubMed DOI

Zeng X. Lu Z. Liu S. Hammond G. B. Xu B. J. Org. Chem. 2017;82:13179–13187. doi: 10.1021/acs.joc.7b02257. PubMed DOI PMC

Sugawara Y. Yamada W. Yoshida S. Ikeno T. Yamada T. J. Am. Chem. Soc. 2007;129:12902–12903. doi: 10.1021/ja074350y. PubMed DOI

Yang L. Zeng Q. Synthesis. 2017;49:3149–3156. doi: 10.1055/s-0036-1588800. DOI

Larock R. C. Reddy C. K. Org. Lett. 2000;2:3325–3327. doi: 10.1021/ol000219i. PubMed DOI

Miyahara Y. Ito Y. N. J. Org. Chem. 2014;79:6801–6807. doi: 10.1021/jo5006137. PubMed DOI