104449-58-3Relevant academic research and scientific papers
UTILISATION DE LA SYNTHESE ATROLACTIQUE POUR L'EVALUATION DE L'EFFICACITE D'INDUCTEURS DE SYNTHESE ASYMETRIQUE.
Hassine, B. Ben,Gorsane, M.,Geerts-Evrard, F.,Pecher, J.,Martin, R. H.,Castelet, D.
, p. 557 - 566 (2007/10/02)
Atrolactic syntheses have been carried out to evaluate the potentiality, in asymmetric syntheses, of chiral inducers.The (dl)-hydroxyhelicenes 1, 2, the (dl) sec. alcohols 3-12 and the (dl)phenolic binaphtyl compound 15 have been used as inducers.The d.e. are collected in table I (6-100percent).The atrolactic asymmetric synthesis has also been carried out using three optically active inducers, namely : (-)-quinine 13, (-)-10,11-dihydroquinine 14, and R(-)-2,2,2-trifluoro-1-(9-anthryl)ethanol 6.Diastereometric and enantiomeric excesses equal or greater than 88percent have been obtained in six cases out of sixteen : (dl)-2-hydroxyheptahelicene 1 (d.e = 100percent +/-2), (1-naphtyl)-(9-anthryl)methanol 3 (d.e = 90percent) ; 2,2,2-trichloro-1-(9-anthryl)ethanol 7 (d.e = 100percent +/-2), 2,2,2-tribromo-1-(9-anthryl)ethanol 8 (d.e = 100percent +/-2), (-)-quinine 13 (e.e = 95.5percent), and (-)-2,2,2-trifluoro-1-(9-anthryl)ethanol 6 (e.e = 88percent).
DIASTEREOSELECTIVE NaBH4 REDUCTIONS OF (dl) α-KETO ESTERS
Ben Hassine, B.,Gorsane, M.,Pecher, J.,Martin, R.H.
, p. 597 - 604 (2007/10/02)
The (dl) α-keto esters 16, were prepared from the (dl) carbinols 1 to 4 and from (dl)-2-hydroxyheptahelicene 5.These (dl) α-keto esters underwent NaBH4 reductions to give the corresponding diastereomeric (dl) α-hydroxy esters 17, with 54 to c.a.100percent diastereomeric excesses.
