ORGN 486 |
| We have investigated a new synthetic methodology for formation of vicinal diamines that is based on aziridine formation. Both alkenes and allenes undergo aziridination with good yield and ring opening of the strained 3-member ring using an amine or an azide occurs with excellent stereoselectivity. In order to maximize the aziridination and minimize the competing reaction of C-H bond insertion, the reaction is efficiently performed using a nitrene that is tethered to the alkene or allene. The regioselectivity for the allene addition is excellent. The aziridines have been shown to undergo regioselective ring opening by reaction with amine, azide, alcohol, sulfide, and iodide. |
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Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |