An enzymatic approach to the desymmetrization of disubstituted pyrrolines.
The enzymatic desymmetrization of 2,2- and 2,5-disubstituted pyrroline compounds is reported in a procedure which gives access to both enantiomers in excellent enantiomeric excess and good yield. The enzyme reaction precursors are formed easily from two readily available substituted pyrroles using both ammonia (Na/NH3) and ammonia-free (Li/DBB) Birch reduction conditions.
Donohoe
Timothy J
TJ
Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Rigby
Caroline L
CL
Thomas
Rhian E
RE
Nieuwenhuys
William F
WF
Bhatti
Farrah L
FL
Cowley
Andrew R
AR
Bhalay
Gurdip
G
Linney
Ian D
ID
D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D011549:Pseudomonas / Q000201:enzymology; D011758:Pyrroles / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D011758:Pyrroles; C013231:pyrroline; D008049:Lipase