Journal
ORGANIC LETTERS
Volume 17, Issue 20, Pages 4988-4991Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02431
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Funding
- Fundamental Research Funds for the Central Universities
- National Natural Science Foundation of China [21172068]
- Shanghai Pujiang Program [14PJD013]
- Shanghai Yangfan Program [14YF1404600]
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A series of chiral N,O-ligands derived from a 1,2-dihydroimidazo[1,2-a]quinolone motif have been evaluated for the asymmetric 1,3-dipolar cydoaddition of azomethine ylides with a novel dipolarophile beta-phthalimidonitroethene. A newly designed DHIPOH ligand 7c bearing 1-methyl and 4-iodo substituents was found to have significant synergistic steric effects and consequently afforded the corresponding 4-nitro-3-aminopyrrolidines with excellent diastereo- (dr up to 98:2) and enantio selectivities (ee up to 99%). Subsequent Raney Ni-catalyzed reduction and deprotection of phthalyl led to the structurally and biologically important 3,4-diaminopyrrolidines in a straightforward and efficient pathway.
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