Enantioselective transformations with diactivated cyclopropanes

ORGN 551

Mukund P. Sibi, Mukund.Sibi@ndsu.edu1, Craig P. Jasperse, jasperse@mhd1.moorhead.msus.edu1, and Zhihua Ma, Zhihua.Ma@ndsu.nodak.edu2. (1) Department of Chemistry, North Dakota State University, Ladd Hall, Fargo, ND 58105, (2) Department of Chemistry and Molecular Biology, North Dakota State University, Ladd Hall, Fargo, ND 58105
We have demonstrated the first examples of chiral Lewis acid catalysis in the formation of oxazines with very high enantioselectivity starting with diactivated cyclopropanes and nitrones (>90% yields and ee). Reactions with racemic substituted cyclopropanes provide 1:1 diastereomeric oxazine products with high enantioselectivity. Results from these experiments along with mechanistic information for the formation of the oxazines will be discussed.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- 201, Oral

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005