Enantioselective Addition Organolithium

Step 1 - Enantioselective Deprotonation

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Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Firstly the isopropyllithium and the Boc-pyrrolidine come together to form a complex with (–)-sparteine. Due to the asymmetric nature of sparteine, the Hs hydrogen is in a position where it is removed by the isopropyllithium, giving the enanteospecific alkyllithium.

Onto Step 2


Animations based on K.B. Wiberg and W.F. Bailey, J. Am. Chem. Soc. 123 (2001), pp. 8231–8238.