Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines

2013 
A tunable and highly regio- and diastereoselective addition of acyclic silyl dienolates 2 to several α-fluoroalkyl sulfinylimines 1 was developed. By appropriate choice of the Lewis acid catalyst, two new chiral α-fluoroalkyl amines 3 and 4 were obtained in good yields and excellent diastereoselectivities (up to >99 : 1 dr), respectively.
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