Miguel Garcia Ruiz - Academia.edu (original) (raw)
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Papers by Miguel Garcia Ruiz
Advanced Synthesis & Catalysis, 2010
The Horner−Wadsworth−Emmons reaction of aldehydes with sulfinimine-derived 3-oxo pyrrolidine phos... more The Horner−Wadsworth−Emmons reaction of aldehydes with sulfinimine-derived 3-oxo pyrrolidine phosphonates represents a new method for the asymmetric synthesis of ring-functionalized cis-2,5-disubstituted 3-oxo pyrrolidines. Enantiopure polyfunctionalized pyrrolidines are found in pharmaceuticals and in numerous natural products. 1 They are also valuable chiral building blocks for the synthesis of more complex derivatives, including the pyrrolizidine and indolizidine alkaloids. 1 Enantiopure pyrrolidines are also useful chiral auxiliaries and ligands for asymmetric syntheses. 2 Although many methods have been reported for the synthesis of pyrrolidines, the continuing challenge is to design more concise methods, particularly enantiopure examples that have ring functionality that can provide access to more complex derivatives. 3 Recent efforts in our group have focused on the asymmetric syntheses of sulfinimine-derived chiral building blocks and the development of related methods for the enantioselective synthesis of amine derivatives, particularly nitrogen heterocycles. 4,5 We require these building blocks to be easily prepared in both enantiomerically pure forms and to provide entry to diverse classes of organonitrogen compounds with a minimum of chemical manipulation and protecting-group chemistry. In this context, we wish to report that 3-oxo pyrrolidine 2-phosphonates and the Horner-Wadsworth-Emmons (HWE) reaction afford enantiopure cis-2,5-disubstituted 3-oxo pyrrolidines that are readily elaborated to functionalized pyrrolidines suitable for further elaboration. Earlier, we introduced an efficient asymmetric synthesis of cis-2,5-disubstituted pyrrolidine phosphonates 4, proline surrogates, via the highly stereoselective intramolecular metal
Advanced Synthesis & Catalysis, 2010
The Horner−Wadsworth−Emmons reaction of aldehydes with sulfinimine-derived 3-oxo pyrrolidine phos... more The Horner−Wadsworth−Emmons reaction of aldehydes with sulfinimine-derived 3-oxo pyrrolidine phosphonates represents a new method for the asymmetric synthesis of ring-functionalized cis-2,5-disubstituted 3-oxo pyrrolidines. Enantiopure polyfunctionalized pyrrolidines are found in pharmaceuticals and in numerous natural products. 1 They are also valuable chiral building blocks for the synthesis of more complex derivatives, including the pyrrolizidine and indolizidine alkaloids. 1 Enantiopure pyrrolidines are also useful chiral auxiliaries and ligands for asymmetric syntheses. 2 Although many methods have been reported for the synthesis of pyrrolidines, the continuing challenge is to design more concise methods, particularly enantiopure examples that have ring functionality that can provide access to more complex derivatives. 3 Recent efforts in our group have focused on the asymmetric syntheses of sulfinimine-derived chiral building blocks and the development of related methods for the enantioselective synthesis of amine derivatives, particularly nitrogen heterocycles. 4,5 We require these building blocks to be easily prepared in both enantiomerically pure forms and to provide entry to diverse classes of organonitrogen compounds with a minimum of chemical manipulation and protecting-group chemistry. In this context, we wish to report that 3-oxo pyrrolidine 2-phosphonates and the Horner-Wadsworth-Emmons (HWE) reaction afford enantiopure cis-2,5-disubstituted 3-oxo pyrrolidines that are readily elaborated to functionalized pyrrolidines suitable for further elaboration. Earlier, we introduced an efficient asymmetric synthesis of cis-2,5-disubstituted pyrrolidine phosphonates 4, proline surrogates, via the highly stereoselective intramolecular metal