A highly stereoselective one-pot intramolecular Mannich reaction using 2-oxopropyl-2-formylbenzoates and anilines as substrates, catalyzed by a secondary amine, has been developed. The procedure leads to a new class of 4-aminoisochromanones bearing two adjacent stereocentres in good yields (up to 85%) with excellent cis-stereoselectivities (dr up to 99:1) and ee values of 92-99%. © Georg Thieme VerlagStuttgart · New York.
Asymmetric organocatalytic synthesis of 4-aminoisochromanones via a direct one-pot intramolecular Mannich reaction / Vetica, Fabrizio; Fronert, Jeanne; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter. - In: SYNTHESIS. - ISSN 0039-7881. - 48:24(2016), pp. 4451-4458. [10.1055/s-0035-1562522]
Asymmetric organocatalytic synthesis of 4-aminoisochromanones via a direct one-pot intramolecular Mannich reaction
Vetica, Fabrizio;
2016
Abstract
A highly stereoselective one-pot intramolecular Mannich reaction using 2-oxopropyl-2-formylbenzoates and anilines as substrates, catalyzed by a secondary amine, has been developed. The procedure leads to a new class of 4-aminoisochromanones bearing two adjacent stereocentres in good yields (up to 85%) with excellent cis-stereoselectivities (dr up to 99:1) and ee values of 92-99%. © Georg Thieme VerlagStuttgart · New York.File | Dimensione | Formato | |
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