112522-06-2Relevant academic research and scientific papers
AN ASYMMETRIC SYNTHESIS OF 4,4- AND 6,6-DIALKYLCYCLOHEXENONES AND 4,4- AND 5,5-DIALKYLCYCLOPENTENONES. APPLICATION TO THE TOTAL SYNTHESIS OF (-)-SILPHIPERFOL-6-ENE
Meyers, A. I.,Lefker, Bruce A.
, p. 5663 - 5676 (2007/10/02)
Chiral amino alcohols have been transformed into bicyclic lactams 1 and 6 which, after metalation and alkylation, gave high diastereomeric ratios of 2,2-dialkyl quaternaly products, 29 and 12, respectively.Addition of organolithium reagents to the carbonyl of these lactams, followed by acidic cleavage, leads to enantiomerically pure cyclohex-2-enones and cyclopent-2-enones.This process was also applied to a key, chiral cyclopentenone 39, which was used by Curran, in racemic form, to prepare the angular triquinane, silphiperfol-6-ene.The total asymmetric synthesis was carried out in 6.6percent yield over nine steps.
AN EFFICIENT ASYMMETRIC SYNTHESIS OF TRISUBSTITUTED CYCLOHEXENONES AND TRISUBSTITUTED CYCLOPENTENONES FROM CHIRAL 2,2-DIALKYL 1,4- AND 1,5-DIKETONES
Meyers, A. I.,Lefker, Bruce A.
, p. 1745 - 1748 (2007/10/02)
Addition of organolithium reagents to the chiral bicyclic lactams 2 and 9 leads to the title compounds in high enantioselectivity.
