1995
DOI: 10.1016/0040-4039(95)00614-i
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Metal-alkene π-chelation: A stereodirecting effect in allylzincation reactions and in zinc mediated cyclopropanations

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Cited by 42 publications
(18 citation statements)
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“…Two scenarios can be imagined, however. The interaction of Zn(II) with unsaturated π-systems has been indicated in the control of stereoselective reactions 61,62. Furthermore, we have recently observed π-interactions between Zn(II) and a C–C double bond in the solid state,63 Bochmann and coworkers have characterized η2-binding of toluene to Zn(C 6 F 5 ) 2 in the solid state,64,65 and Vigalok and coworkers presented solid state and solution evidence for Zn(II) interactions with alkyne π-systems 66.…”
Section: Resultsmentioning
confidence: 99%
“…Two scenarios can be imagined, however. The interaction of Zn(II) with unsaturated π-systems has been indicated in the control of stereoselective reactions 61,62. Furthermore, we have recently observed π-interactions between Zn(II) and a C–C double bond in the solid state,63 Bochmann and coworkers have characterized η2-binding of toluene to Zn(C 6 F 5 ) 2 in the solid state,64,65 and Vigalok and coworkers presented solid state and solution evidence for Zn(II) interactions with alkyne π-systems 66.…”
Section: Resultsmentioning
confidence: 99%
“…The dramatic effects of conjugated enynes on reactivity and regioselectivity are not consistent with a purely steric and/or electronic phenomenon. Tethered alkenyl groups in enynes and dienes are also known to increase the reactivity and regioselectivity of transition metal-catalyzed coupling reactions 11. The directing effects of tethered alkenyl groups are usually explained by coordination with the metal center during the rate- and regioselectivity-determining step, since the length of tether has dramatic effects on the reactivity and regioselectivity of enynes.…”
Section: Introductionmentioning
confidence: 99%
“…58,59 One such example is the allylzincation reaction shown in Scheme 1. 58, 59 The high degree of acyclic stereocontrol observed was explained by coordination of the pendent olefin to zinc.…”
Section: Introductionmentioning
confidence: 99%