Stereoselectivity in metal carbene and Lewis acid-catalyzed reactions from diastereomeric dirhodium(II) carboxamidates: Menthyl N-acetyl-2-oxoimidazolidine-4(S)-carboxylates |
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| Institution: | 1. Department of Organic Chemistry and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Faculty of Sciences, University of Alicante, E-03080 Alicante, Spain;2. Instituto de Síntesis Orgánica, Faculty of Sciences, University of Alicante, Spain;1. Departamento de Veterinária, Universidade Federal de Viçosa, Viçosa, MG, Brazil;2. Departamento de Veterinária, Universidade Vila Velha, ES, Brazil;3. Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Viçosa, Viçosa, MG, Brazil;4. Departamento de Parasitologia Animal, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil;1. State Key Laboratory of Complex System Simulation, Beijing Institute of System Engineering, Beijing, China;2. Dept. of Computer Engineering, University of Cádiz, Cádiz, Spain;3. IRIDIA, CoDE, Université Libre de Bruxelles (ULB), Brussels, Belgium;1. Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-901 Ribeirão Preto, SP, Brazil;2. Inst. of Chemistry – São Paulo State University- UNESP, 14801-970 Araraquara, SP, Brazil;3. Department of Morphology, Dental School at Araraquara, Univ. Estadual Paulista – UNESP, Araraquara, SP, Brazil;1. Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Univesitaria, Circuito Exterior, Coyoacán 04510, Ciudad de México, Mexico;2. Laboratorio de Síntesis de Complejos, Facultad de Ciéncias Químicas, Universidad Autónoma de Puebla, A. P. 1067, 72001 Puebla, Pue., Mexico |
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| Abstract: | The influence of a chiral menthyl group as the pendant ester substituent on the N-acetyl-2-oxoimidazolidine-4S-carboxylate ligands in chiral dirhodium(II) imidazolidinone catalysts has been examined. Significant match/mismatch influences are evident in the observed stereocontrol for carbon–hydrogen insertion reactions with diazoacetates, but these effects are minimal in cyclopropanation reactions. Steric restrictions prevent effective enantiocontrol in hetero-Diels–Alder reactions using these menthyl-substituted catalysts. |
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