Unprecedented noncatalyzed anti-carbozincation of diethyl acetylenedicarboxylate through alkylzinc group radical transfer

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1884-1887

  Maury, Julien ^a   Feray, Laurence ^a   Bertrand, Michèle P ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953197250     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200419x     Document Type: Article

References (48)

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39. Vinylzinc are usually prepared through transmetalation of differents vinylmetal. Here are selected examples: for transmetalation involving vinylnickel species, see: Stüdemann, T.; Ibrahim-Ouali, M.; Knochel, P. Tetrahedron 1998, 54, 1299-1316 For alkene transfer from zirconium to zinc, see: Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761-768 For transmetalation involving vinyllithium species, see: Agami, C.; Couty, F.; Evano, G. Org. Lett. 2000, 2, 2085-2088
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42. The addition of allylzinc bromide to acetylenic sulfone without any additive such as copper salt was reported, see: Xie, M.; Wang, J.; Gu, X.; Sun, Y.; Wang, S. Org. Lett. 2006, 8, 431-434 Direct carbozincation reaction of trifluoromethylated acetylenic phosphonates mediated by dialkylzinc was also reported, see: Konno, T.; Morigaki, A.; Ninomiya, K.; Miyabe, T.; Ishihara, T. Synthesis 2008, 564-572. In these cases, a vinylzinc was formed in alpha position to an electronwithdrawing group
43. The formation of a zinc allenoate intermediate cannot be ruled out. We assume that the coordination of the zinc atom to the carboxylate stabilizes the vinylzinc intermediate and therefore displaces the equilibrium toward the latter. This explains the high stereoselectivity of the reaction whatever the bulk of the alkyl group is.
44. 4Cl. Whatever the conditions (with or without the alkyliodide) the E -isomer was deuterated up to 95% whereas the traces of Z- isomer remained non deuterated.
45. 2 under sunlamp irradiation, the addition of t- BuI and i- PrI to DMAD led to the formation of fumaric and maleic adducts in 76:24 and 16:84 relative ratios, respectively, see ref 13a.
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47. When DMAD was reacted with selenoborane, the authors concluded that the intermediate formed was not a vinylborane but a vinyl radical, see: Kataoka, T.; Yoshimatsu, M.; Shimizu, H.; Hori, M. Tetrahedron Lett. 1990, 31, 5927-5930
48. The E / Z ratio was more or less the same as the one reported by Curran under standard iodine atom transfer radical addition of t- butyl iodide to DMAD, see ref 13a.