Enantioselective Addition Organolithium Step 1

Step 1 – Enantioselective Deprotonation
Sn2

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 enantiospecific alkyllithium.

Onto Step 2

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

 

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