Stereochemistry of the SN2′ reaction with acyclic allylic esters
Abstract
Aminolysis of (R)- or (S)-α-methyl[γ-2H]allyl (1) or α-n-pentyl[γ-2H]allyl (2) 2,6-dichlorobenzoates with (R)- or (S)-α-methylbenzylamine (3) favours syn over anti displacement by a factor of 1·4–1·8.