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 b...

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Veröffentlicht in:	Journal of organic chemistry 2006-08, Vol.71 (16), p.6298-6301
Hauptverfasser:	Donohoe, Timothy J, Rigby, Caroline L, Thomas, Rhian E, Nieuwenhuys, William F, Bhatti, Farrah L, Cowley, Andrew R, Bhalay, Gurdip, Linney, Ian D
Format:	Artikel
Sprache:	eng
Schlagworte:	Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Chemistry Exact sciences and technology Fundamental and applied biological sciences. Psychology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Lipase - metabolism Methods. Procedures. Technologies Molecular Structure Organic chemistry Preparations and properties Pseudomonas - enzymology Pyrroles - chemistry Pyrroles - metabolism Stereoisomerism
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo060926a