New Ferrocenyl Chiral Auxiliary Substituents for Amines. Applications to Syntheses of Mossambine and Vinblastine
The Journal of Organic Chemistry2001Vol. 66(5), pp. 1560–1566
Citations Over Time
Abstract
(+)-(R)-1,2-(alpha-(R)-Mesyloxy-beta-dimethyltetramethylene)-ferrocene was synthesized and used as a chiral auxiliary for N-alkylation of methyl 1,2,3,4,5,6-hexahydroazepino[4,5-b] indole-5-xi-carboxylates. Condensation with aldehydes then provided tetracyclic products in a diastereomeric ratio of at least 97:3. Gentle cleavage in acetic acid removed the chiral auxiliary to give the corresponding secondary amines in >99% ee. Thus, key intermediates leading to mossambine and vinblastine could be synthesized with high enantioselectivity. The enantioselectivity greatly exceeds that found with other chiral N-auxiliaries developed in our studies.
Related Papers
- → Diastereoselective Synthesis of cycloSaligenyl‐Nucleosyl‐Phosphotriesters(2010)19 cited
- → An efficient synthetic method for optically pure heterohelicenes(1992)21 cited
- → Resolution of synthetically useful myo-inositol derivatives using the chiral auxiliary O-acetylmandelic acid(2004)8 cited
- → Synthesis of chiral 1-(imidazol-2-yl)alkanamines using neomenthanethiol as a chiral auxiliary(2016)2 cited
- (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation(2015)