Financial support has been provided by the National Science Foundation (predoctoral fellowship to G.B.) and the National Institutes of Health (postdoctoral fellowship to K.A.S., GM 43912-11 and GM 33328-18).
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Communication
Remarkably Stable Tetrahedral Intermediates: Carbinols from Nucleophilic Additions to N–Acylpyrroles†
Article first published online: 30 AUG 2002
DOI: 10.1002/1521-3773(20020902)41:17<3188::AID-ANIE3188>3.0.CO;2-H
© 2002 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
41:17<>1.0.CO;2-C/asset/cover.gif?v=1&s=930ebca81f4d0a27f052cbcdba3757b263c6c1e1 "Angewandte Chemie International Edition")
Angewandte Chemie International Edition
Volume 41, Issue 17, pages 3188–3191, September 2, 2002
Additional Information
How to Cite
Evans, D. A., Borg, G. and Scheidt, K. A. (2002), Remarkably Stable Tetrahedral Intermediates: Carbinols from Nucleophilic Additions to N–Acylpyrroles. Angewandte Chemie International Edition, 41: 3188–3191. doi: 10.1002/1521-3773(20020902)41:17<3188::AID-ANIE3188>3.0.CO;2-H
- †
Publication History
- Issue published online: 30 AUG 2002
- Article first published online: 30 AUG 2002
- Manuscript Received: 22 MAY 2002
Keywords:
- carbinols;
- nitrogen heterocycles;
- nucleophilic addition;
- reaction intermediates;
- reaction mechanisms
Graphical Abstract
41:17<3188::AID-ANIE3188>3.0.CO;2-H/asset/image_m/mcontent.gif?v=1&s=ab0787b2aa8128faabff1c5a508f34293eb1ea5a "Thumbnail image of graphical abstract")
Sufficiently stable intermediates formed in the reaction of N-acylpyrroles (1) with hydride and Grignard reagents can undergo further synthetic transformations and chromatographic purification to enable the generation of pyrrolecarbinols 2 in 76–95 % yields [Eq. (1)].