Enantioselective chemoenzymatic synthesis of trans-aziridines.
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.
Ritzen
Bas
B
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
van Oers
Matthijs C M
MC
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
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
D000447:Aldehydes; D001388:Aziridines; D009942:Organometallic Compounds; D000446:Aldehyde-Lyases; C087495:acetone-cyanohydrin lyase