NDLI: Synthesis of Pyrroles via [3,3]-Rearrangement and Paal-Knorr Reaction

Content Provider	Scilit
Editor	Wang, H. -Y. Mueller, D. S. Sachwani, R. M. Londino, H. N. Anderson, L. L.
Copyright Year	2010
Description	Reported is the synthesis of 2,4- and 2,3,4-substituted pyrroles via [3,3]-sigmatropic rearrangement and subsequent Paal-Knorr reaction. The iridium-catalyzed isomerization products 1 were isolated with vinyl E/Z ratios of approximately 1:2. The Paal-Knorr intermediate A was identified by NMR spectroscopy. The target pyrroles may also be afforded in a one-pot reaction in yields comparable to those obtained in the two-step procedure. Interestingly, as long as $R^{²}$ = CN, the reaction proceeded directly from O-allyl oximes to pyrroles without the need for molecular sieves at lower temperature (25 ˚C).
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0030-1257846.pdf
Ending Page	0878
Page Count	1
Starting Page	0878
ISSN	18611958
e-ISSN	1861194X
DOI	10.1055/s-0030-1257846
Journal	Synfacts
Issue Number	08
Volume Number	2010
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2010-07-22
Access Restriction	Open
Subject Keyword	Journal: Synfacts Organic Chemistry
Content Type	Text
Resource Type	Article

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Synthesis of Pyrroles via [3,3]-Rearrangement and Paal-Knorr Reaction