Synthesis of (E)-α,β-unsaturated esters with total diastereoselectivity by using chromium dichloride
Synthesis of di- and trisubstituted (E)-α,β-unsaturated esters is easily achieved by using chromium dichloride through an elimination reaction of a diastereoisomeric mixture of α-halo-β-hydroxy esters. The starting materials were easily prepared by the aldol reaction of lithium enolates of α-chloroesters with aldehydes. A mechanism to explain this elimination process is proposed.
Concellón, José M.,Rodríguez-Solla, Humberto,Méjica, Carmen
An efficient synthesis of (E)-α,β-unsaturated ketones and esters with total stereoselectivity by using chromium dichloride
(E)-α,β-Unsaturated ketones 1 or esters 2 can be obtained with complete stereoselectivity by reaction of different 2-chloro-3-hydroxy ketones 3 or esters 4 and CrCl2. A comparative study of the results of synthesis of ketones 1 with CrCl2 or samarium is performed. A mechanism to explain both β-elimination reactions has been proposed.
Concellón, José M.,Rodríguez-Solla, Humberto,Méjica, Carmen
p. 3292 - 3300
(2007/10/03)
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