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Abstract
One-pot synthesis of optically active 1,4-disubstituted-3-carbamoyl-azetidinones from 5-[(N-arylamino)- (hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines is achieved via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition. Three possible chiral induction approaches were tested and (R)-(+)-1-phenylethylamine was confirmed as the best chiral auxiliary. Among the four possible diastereoisomers, only two with significant excess of one were formed
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Authors (3)
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Zakaszewska Anna Mgr inż
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Najda Ewelina Mgr inż
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- Accepted or Published Version
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- Copyright (Royal Society of Chemistry 2017)
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
NEW JOURNAL OF CHEMISTRY
no. 41,
edition 6,
pages 2479 - 2489,
ISSN: 1144-0546 - Language:
- English
- Publication year:
- 2017
- Bibliographic description:
- Anna Z., Ewelina N., Makowiec S.: A new approach to the stereoselective synthesis of trans-3-carbamoyl-b-lactam moieties†// NEW JOURNAL OF CHEMISTRY. -Vol. 41, iss. 6 (2017), s.2479-2489
- DOI:
- Digital Object Identifier (open in new tab) 10.1039/c7nj00445a
- Verified by:
- Gdańsk University of Technology
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