NDLI: NHC-Catalyzed β-Lactam Synthesis

Content Provider	Scilit
Copyright Year	2008
Description	Carbene catalysis has been applied to the highly enantio- and diastereoselective synthesis of bicyclic β-lactams. 3-Alkyl or 3-aryl enals 1 and chalcone-derived N-sulfonyl imines 2 are used as starting materials. Chiral triazolium precatalyst 3 (10 mol%) together with either DBU (for aliphatic enals) or DMAP (for aromatic enals) as catalytic base were sufficient to afford cyclopentyl-fused β-lactams 4 in good yields and with excellent enantioselectivities. In the case of 3-alkyl enals 1, only a single diastereomer was formed. The authors propose a tandem crossed-aza-benzoin/oxy-Cope reaction as the key bond-forming step.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2008-1042727.pdf
Ending Page	0307
Page Count	1
Starting Page	0307
ISSN	18611958
e-ISSN	1861194X
DOI	10.1055/s-2008-1042727
Journal	Synfacts
Issue Number	03
Volume Number	2008
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2008-02-21
Access Restriction	Open
Subject Keyword	Journal: Synfacts Organic Chemistry Β Lactams Em Class
Content Type	Text
Resource Type	Article

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NHC-Catalyzed β-Lactam Synthesis