Enantio- and diastereo-selective synthesis of pipecolic acid derivatives using the aza-Diels–Alder reaction of imines with dienes
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1337-1340
- https://doi.org/10.1039/p19910001337
Abstract
Optically active pipecolic acid derivatives can be prepared by the aza- Diels–Alder reaction of simple dienes with the imine derived from ethyl glyoxylate and chiral 1-phenylethylamine; the cycloadditions are regiospecific, highly diastereoselective within the heterocyclic ring (>92%exo with cyclic dienes, and 100%endo with acyclic dienes), and lead to high asymmetric induction in most cases (average d.e. = 72%).Keywords
This publication has 24 references indexed in Scilit:
- Hetero-Diels-Alder reactions on a carbohydrate template: stereoselective synthesis of (S)-anabasinThe Journal of Organic Chemistry, 1989
- Carbohydrates as Chiral Templates: Stereoselective Tandem Mannich‐Michael Reactions for the Synthesis of Piperidine AlkaloidsAngewandte Chemie International Edition in English, 1989
- Asymmetrische Hetero‐Diels‐Alder‐Reaktionen in wäßriger Lösung unter Verwendung von Aminosäureestern als chiralen AuxiliarenEuropean Journal of Organic Chemistry, 1989
- The Synthesis of Natural Heterocyclic Products by Hetero Diels-Alder Cycloaddition ReactionsPublished by Elsevier ,1987
- Aza Diels-Alder reactions in aqueous solution: cyclocondensation of dienes with simple iminium salts generated under Mannich conditionsJournal of the American Chemical Society, 1985
- Alkaloid total synthesis by intramolecular imino Diels-Alder cycloadditionsAccounts of Chemical Research, 1985
- Synthetic aspects of diels-alder cycloadditions with heterodienophilesTetrahedron, 1982
- Synthesis of Nitrogen-containing Heterocycles by the Imino Diels-Alder ReactionHETEROCYCLES, 1979
- Heterodienophiles 9. On the preference forTetrahedron Letters, 1978
- Heterocyclen durch Diensynthese, II: N‐[Butyloxycarbonylmethylen]‐p‐toluolsulfonamid, ein neues Dienophil zur Darstellung von Pyridin‐, Piperidein‐ und Piperidin‐Derivaten durch Diels‐Alder‐SyntheseEuropean Journal of Inorganic Chemistry, 1965