Asymmetric synthesis of isoquinuclidines by Diels–Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst

The chiral isoquinuclidine derivative, 2-azabicyclo[2.2.2]octane ring system, endo-(7 R)- 3 was obtained in good yield with excellent diastereoselectivity (up to 92% de) by Diels–Alder reaction of 1-(phenoxycarbonyl)-1,2-dihydropyridine 1 with N-acryloyl-(4 S)-4-benzyloxazolidin-2-one (4 S)- 2 using...

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Veröffentlicht in:	Tetrahedron 2012-02, Vol.68 (6), p.1774-1781
Hauptverfasser:	Seki, Chigusa, Hirama, Masafumi, Hutabarat, N.D.M. Romauli, Takada, Junko, Suttibut, Chonticha, Takahashi, Hideto, Takaguchi, Takuya, Kohari, Yoshihito, Nakano, Hiroto, Uwai, Koji, Takano, Nobuhiro, Yasui, Mitsukuni, Okuyama, Yuko, Takeshita, Mitsuhiro, Matsuyama, Haruo
Format:	Artikel
Sprache:	eng
Schlagworte:	1,2-Dihydropyridine 2-Azabicyclo[2.2.2]octane Alkaloid Asymmetry Catalysis Catalysts Catalysts: preparations and properties Chemistry Chiral Lewis acid catalyst Derivatives Diels-Alder reactions Diels–Alder reaction Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Lewis acid Organic chemistry Preparations and properties Reactivity and mechanisms Solvents Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Toluene
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