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Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived Ligands

Guilherme S. Caleffi, Olatz Larrañaga,  Marcos Ferrándiz-Saperas, Paulo R. R. Costa, Carmen Nájera*, Abel de Cózar, Fernando P. Cossío*, José M. Sansano*

*Centro de Innovación en Química Avanzada (ORFEO-CINQA), 08193 Barcelona, Spain, Email: cnajeraua.es, fp.cossioehu.es, jmsansanoua.es

G. S. Caleffi, O. Larrañaga, M. Ferrándiz-Saperas, P. R. R. Costa, C. Nájera, A. de Cózar, F. P. Cossío, J. M. Sansano, J. Org. Chem., 2019, 84, 10593-10605.

DOI: 10.1021/acs.joc.9b00267 (free Supporting Information)


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Abstract

Depending on the use of copper(I) and silver(I) complexes with (S)-DM- or (S)-DTBM-Segphos as ligands, a catalytic enantioselective 1,3-dipolar cycloaddition between imino esters and electrophilic alkenes provides diastereodivergently exo- or endo-cycloadducts. Functional groups of the dipolarophile and the choice of the catalyst play an important role in promoting reverse diastereoselectivities.

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diastereoselectivity rationale



Key Words

1,3-dipolar cycloaddition, pyrrolidines


ID: J42-Y2019