ChemInform Abstract: Enantioselective Synthesis of Polysubstituted Spiro-nitroprolinates Mediated by a (R,R)-Me-DuPhos·AgF-Catalyzed 1,3-Dipolar Cycloaddition

Autor:	José M. Sansano, Ricardo Ortiz, Carmen Nájera, Abel de Cózar, Alberto Cayuelas, Olatz Larrañaga, Fernando P. Cossío
Rok vydání:	2016
Předmět:	chemistry.chemical_compound Chemistry 1 3-Dipolar cycloaddition Enantioselective synthesis Absolute configuration Azomethine ylide Density functional theory General Medicine DuPhos Medicinal chemistry Catalysis Bifunctional catalyst
Zdroj:	ChemInform. 47
ISSN:	0931-7597
DOI:	10.1002/chin.201644097
Popis:	The synthesis of constrained spirocycles is achieved effectively by means of 1,3-dipolar cyclodditions employing α-imino γ-lactones as azomethine ylide precursors and nitroalkenes as dipolarophiles. The complex formed by (R,R)-Me-DuPhos 18 and AgF is the most efficient bifunctional catalyst. Final spiro-nitroprolinates cycloadducts are obtained in good to moderate yields and both high diastereo- and enantioselectivities. Density functional theory (DFT) calculations supported the expected absolute configuration as well as other stereochemical parameters.
Databáze:	OpenAIRE
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