C O M M U N I C A T I O N S
Table 1. Diastereoselective and Enantioselective
Cyclopropanation of Electron-Deficient Olefins Catalyzed by
[Co(1)]a
Table 2. Solvent Effect in [Co(1)]-Catalyzed Diastereoselective
and Enantioselective Cyclopropanation of Electron-Deficient
Olefinsa
a Performed at rt for 20 h using 1 mol % of [Co(1)] under N2 with 1.0
equiv of alkene and 1.2 equiv of t-BDA in the presence of 0.5 equiv of
DMAP; [alkene] ) 0.25 M. b Isolated yields. c The trans:cis ratios were
determined by GC. d The ee of trans isomer was determined by GC or HPLC
on chiral stationary phase.
have different reactivity characteristics from the previously reported
Cu(I)- or Rh(II)2-based systems. Efforts are underway to further
improve the substrate generality, product selectivity, and process
practicality of the catalytic system.
Acknowledgment. We are grateful to UTK and USF (Startup
Funds), ACS-PRF (AC Grant), NSF (CAREER Award), and NSF
(CRIF:MU-0443611, Mass Facility) for financial support.
Supporting Information Available: Experimental procedures and
analytical data for all compounds. This material is available free of
References
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a Performed in toluene at rt for 20 h using 1 mol % of [Co(1)] under N2
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selectivity toward styrene derivatives shown previously,13 [Co(1)]
may be considered one of the most selective catalysts for asym-
metric cyclopropanation of both electron-sufficient and electron-
deficient olefins with diazoacetates.1-5 These results suggest that
the catalytic intermediate of the current Co(II)-based system may
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