Novel metal-free, readily available chiral catalytic systems for the enantioselective reduction of keto imines are reported. Different β-imino esters were reduced by trichlorosilane in the presence of 10 mol% of a chiral Lewis base easily obtained in one step only from prolinol, in high yields and in up to 85% enantioselectivity; imines bearing an inexpensive and removable chiral auxiliary, were reduced with complete control of the absolute stereochemistry. The methodology was successfully extended to the stereoselective synthesis of α-amino esters.
New, readily available organocatalysts for the enantioselective reduction of alfa imino- and beta-imino esters / M. Bonsignore, M. Benaglia, R. Annunziata, G. Celentano. - In: SYNLETT. - ISSN 0936-5214. - 2011:8(2011), pp. 1085-1088. [10.1055/s-0030-1259941]
New, readily available organocatalysts for the enantioselective reduction of alfa imino- and beta-imino esters
M. BonsignorePrimo
;M. BenagliaSecondo
;R. AnnunziataPenultimo
;G. CelentanoUltimo
2011
Abstract
Novel metal-free, readily available chiral catalytic systems for the enantioselective reduction of keto imines are reported. Different β-imino esters were reduced by trichlorosilane in the presence of 10 mol% of a chiral Lewis base easily obtained in one step only from prolinol, in high yields and in up to 85% enantioselectivity; imines bearing an inexpensive and removable chiral auxiliary, were reduced with complete control of the absolute stereochemistry. The methodology was successfully extended to the stereoselective synthesis of α-amino esters.Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.