title: Enantioselective chemoenzymatic synthesis of trans-aziridines.
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.
authors.affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
authors.forename: Bas
authors.initials: B
authors.lastname: Ritzen
authors.forename: Matthijs C M
authors.initials: MC
authors.lastname: van Oers
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
mesh_terms: D000446:Aldehyde-Lyases / Q000737:chemistry / Q000378:metabolism*; D000447:Aldehydes / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001388:Aziridines; D009942:Organometallic Compounds; D000446:Aldehyde-Lyases; C087495:acetone-cyanohydrin lyase