Enantioselective Addition Organolithium

Step 1 - Enantioselective Deprotonation

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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


K. B. Wiberg and W. F. Bailey, J. Am. Chem. Soc., 2001, 123, 8231–8238.