A C2‐Chiral Bis(amidinium) Catalyst for a Diels−Alder Reaction Constituting the Key Step of the Quinkert−Dane Estrone Synthesis
- 10 April 2003
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2003 (9) , 1661-1664
Abstract
A novel C2‐chiral bis(amidinium) salt 12 has been synthesised from 5‐(tert‐butyl)isophthalic acid. The hydrogen‐bond‐mediated association of dienophiles 3a and 3b with the chiral host molecule 12 accelerates the Diels−Alder reactions with diene 2 by more than three orders of magnitude. In addition, enantioselective formation of the desired adducts is observed under catalysis with 12. Good ratios of 4a(b) + ent‐4a(b)/5a(b) + ent‐5a(b) from 1:10 to 1:22 were found in all reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Keywords
This publication has 18 references indexed in Scilit:
- Catalysis of a Diels−Alder Reaction by Amidinium IonsThe Journal of Organic Chemistry, 2000
- Branched non-covalent complexes between carboxylic acids and two tris(amidines)Journal of the Chemical Society, Perkin Transactions 1, 1999
- Synthesis of Enantiopure Estrone via a Double Heck ReactionJournal of the American Chemical Society, 1998
- Star-branched non-covalent complexes between carboxylic acids and a tris(imidazoline) baseChemical Communications, 1998
- Total Synthesis with a Chirogenic Opening Move Demonstrated on Steroids with Estrane or 18a‐Homoestrane SkeletonHelvetica Chimica Acta, 1995
- Synthesis of Enantiopure C2-Chiral AmidinesSynthesis, 1995
- Stereoselektive Synthese enantiomerenreiner Naturstoffe — Beispiel ÖstronAngewandte Chemie, 1983
- Condensation of 1-Vinyl-6-methoxy-3,4-dihydronaphthalene and 3-Methyl-3-cyclopentene-1,2-dione. Structure of Dane's AdductJournal of the American Chemical Society, 1956
- Synthesen in der hydroaromatischen Reihe. V. Die Synthese eines Isomeren des ÖstronsEuropean Journal of Organic Chemistry, 1939
- Synthesen in der hydroaromatischen Reihe. IV. 1. Die Kondensation von 1‐Methyl‐cyclopenten‐dion‐2,3 mit 1‐Vinyl‐6‐methoxy‐3,4‐dihydro‐naphtalin. 2. Darstellung und Diensynthesen von 3‐Oxy‐2,6‐dimethyl‐benzochinon‐(1,4)European Journal of Organic Chemistry, 1938