Enantioselective Chemoenzymatic Synthesis of trans-Aziridines
The Journal of Organic Chemistry2009Vol. 74(19), pp. 7548–7551
Citations Over TimeTop 14% of 2009 papers
Abstract
A straightforward, five-step procedure for the synthesis of enantiomerically pure 2,3-disubstituted trans-aziridines has been developed starting from commercially available aldehydes. Hydroxynitrile lyase-mediated cyanohydrin formation provided cyanohydrins in excellent enantioselectivities and good yields. Subsequent formation of diastereomerically pure anti-amino alcohols via a one-pot Grignard addition-reduction sequence, Cu(II)-catalyzed diazotransfer, and triphenylphosphine-mediated reductive cyclization provided the corresponding trans-aziridines in good yields and excellent diastereoselectivities.
Related Papers
- → Organocatalysis in Radical Chemistry. Enantioselective α-Oxyamination of Aldehydes(2007)294 cited
- → Optimisation of the Enantioselective Synthesis of Cyanohydrin Esters(2005)61 cited
- → ChemInform Abstract: Chemistry of Polyhalogenated Nitrobutadienes. Part 7. A Novel Synthetic Access to Chlorinated Nitrile Oxides.(2009)1 cited
- → Synthesis of Perfluoroalkyl‐Substituted Bis(oxazolines) as Ligands for Catalytic Enantioselective Reactions.(2003)
- → ChemInform Abstract: Catalytic Enantioselective Allylation of Carbonyl Compounds and Imines(2012)