An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines

An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles was successfully achieved via Pd-catalyzed intramolecular C–N bond formation between the nitrogen originated from the aziridine and the halogen containing aromatic carbon. This reaction has a broad substrate sco...

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Bibliographic Details
Published in:Tetrahedron 2010-10, Vol.66 (40), p.8108-8114
Main Authors: Chan Kim, Jong, Choi, Hwan Geun, Kim, Min Suk, Ha, Hyun-Joon, Lee, Won Koo
Format: Article
Language:English
Subjects:
Benzoxazine
Chemistry
Chiral aziridine
C–N bond formation
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Tetrahydroquinoline
Tetrahydroquinoxaline
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Summary:An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles was successfully achieved via Pd-catalyzed intramolecular C–N bond formation between the nitrogen originated from the aziridine and the halogen containing aromatic carbon. This reaction has a broad substrate scope to provide various enantiomerically pure (3,4-dihydro-2 H-benzo[ b][1,4]oxazin-3-yl)methanols, 2-hydroxymethyl-1,2,3,4-tetrahydroquinolines and (1,2,3,4-tetrahydroquinoxalin-2-yl)methanols from common chiral aziridines in good yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.07.027