Guillena, Gabriela, Hita López, María del Carmen, Nájera, Carmen
Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols
GUILLENA TOWNLEY, Gabriela; HITA, María del Carmen; NÁJERA DOMINGO, Carmen. "Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols". Tetrahedron: Asymmetry. Vol. 17, Issue 7 (3 Apr. 2006). ISSN 0957-4166, pp. 1027-1031
URI: http://hdl.handle.net/10045/2507
DOI: 10.1016/j.tetasy.2006.03.023
ISSN: 0957-4166
Abstract: 
Recoverable BINAM-prolinamide derivatives, as well as L-proline, give results complementary to antibodies when used as
organocatalysts for aldol eactions between aldehydes and α-alkoxyacetones driving regioselectively to anti/syn-1,2-diols. The formation of the iso-regioisomer is suppressed using α-hydroxyacetone in DMSO at rt, achieving the corresponding anti-1,2-diol with ee’s up to 85%. For α-alkoxyacetones (methoxy, benzyloxy, and tert-butyldimethylsilyloxy), the highest regio- and diastereoselectivity is achieved using α-methoxyacetone in DMF at 0 °C; the enantiomeric excess for the anti-1,2-isomer being up to 98%.
Keywords:Organocatalysis, Aldol, Enantioselective, Asymmetric synthesis, Amino acids, Proline
Elsevier
info:eu-repo/semantics/article