The first enantioenriched metalated nitrile possessing macroscopic configurationat stability
Figure presented Magnesium - bromine exchange on enantiopure cyclopropyl bromonitrile 5 at -100°C for 1 min followed by a D2O quench gives the deuterionitrile in 81% ee (retention); additional trapping experiments establish t1/2(rac) = 11.4 h at -100°C. These experiments provide the first glimpse into the stereochemical aspects of Mg-Br exchange. The intermediate formed is the first metalated nitrile demonstrated to possess macroscopic configurational stability.
Carlier, Paul R.,Zhang, Yiqun
p. 1319 - 1322
(2007/12/29)
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