Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis.
We report a new catalyst system that should enhance the use of enantioselective 1,3-dipolar cycloadditions of azomethine ylides with electronic-deficient olefins in the divergent pathways of diversity-oriented synthesis (DOS). The underlying reaction is of considerable interest in DOS because its stereospecificity enables stereochemical diversification of up to four tetrahedral centers on pyrrolidine rings. This new catalyst system extends the scope and selectivity of the azomethine ylide cycloaddition and is compatible with reagents used in a one-bead/one-stock solution technology platform for DOS.
Chen
Chuo
C
Department of Chemistry and Chemical Biology, Howard Hughes Medical Institute, , Institute of Chemistry and Cell Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Li
Xiaodong
X
Schreiber
Stuart L
SL
D000447:Aldehydes / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis*; D007098:Imino Acids / Q000138:chemical synthesis*
D000447:Aldehydes; D001391:Azo Compounds; D004952:Esters; D007098:Imino Acids; C001825:azomethane