AI Article Synopsis
- A new method for synthesizing alpha-hydrazino ketones is presented, utilizing manganese enolates and enamines in reactions with azodicarboxylate esters.
- The process is regioselective, yielding the desired products in good to excellent yields, focusing on kinetic alpha-hydrazino ketones.
- Using enantiopure N-sulfinyl manganese enamines resulted in stereoselectivity varying between 40% to 68% enantiomeric excess (ee).
Article Abstract
A straightforward procedure for the regio- and stereoselective synthesis of alpha-hydrazino ketones is described. Manganese enolates and manganese enamines derived from ketones and from the corresponding N-sulfinylimines react with azodicarboxylate esters (DTBAD and DEAD) in a regioselective fashion to afford in good to excellent yields the kinetic alpha-hydrazino ketones as sole or highly prevalent products. When enantiopure N-sulfinyl manganese enamines were used the stereoselectivity of these reactions ranged from 40% to 68% ee.
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| http://dx.doi.org/10.1021/jo049152t | DOI Listing |
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