Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 24, Pages 12426-12439Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402075d
Keywords
-
Categories
Funding
- NSF Chemical Instrumentation Program [CHE-9700278]
Ask authors/readers for more resources
Organozincates or Grignard reagents in the presence of zinc catalysts undergo Michael initiated ring closure (MIRC) reactions with gamma,delta-epoxy-alpha,beta-enoates, enones, enesulfones, and enamides to afford 1,2,3-trisubstituted cyclopropanes. The direction of diastereoselectivity is solvent dependent for alkyl Grignard reagents reacting with epoxy enoates, ensulfones, and enamides but solvent independent for the enones. Excellent diastereoselectivity can be achieved for the epoxy enoates, enones, and ensulfones, while the enamides afford modest diastereoselectivity under optimal conditions. The MIRC reaction can be achieved with phenylmagnesium chloride and these substrates under reaction conditions designed to minimize biphenyl formation.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available