✦ LIBER ✦
Asymmetric bridging annulation reaction involving the intramolecular conjugate addition of chiral imines to enoates: Access to a polycyclic system related to the taxane core
✍ Scribed by Christian Cavé; Sophie Boggero; Ramon Casas; Françoise Dumas; Jacqueline Mahuteau; Jean d'Angelo
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 232 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0957-4166
No coin nor oath required. For personal study only.
✦ Synopsis
R )-l-phenylethylamine-induced cyclization of ketoenoate 2 4 led to a 2:1 mixture of "all-cis" polycyclic adducts 2 5 and 2 6, structurally related to the taxane series.
Ten years ago, we reported that chiral imines 3, derived from racemic 2-alkylcyclanones 1 and optically active 1-phenylethylamine 2, add, under neutral conditions, to electrophilic alkenes 4 leading, after hydrolytic work-up, to 2,2-dialkylcyclanones 5 with a good yield and excellent regio-and stereoselectivity. 2
4
~ EWG