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

  • Kim, Jong Chan
  • Choi, Hwan Geun
  • Kim, Min Suk
  • Ha, Hyun-Joon
  • Lee, Won Koo
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초록

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-2H-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. (C) 2010 Elsevier Ltd. All rights reserved.

키워드

Chiral aziridineTetrahydroquinolineBenzoxazineTetrahydroquinoxalineC-N bond formation1,4-BENZOXAZINE DERIVATIVESPOTENTQUINOXALINEAMINATIONANALOGS
제목
An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines
저자
Kim, Jong ChanChoi, Hwan GeunKim, Min SukHa, Hyun-JoonLee, Won Koo
DOI
10.1016/j.tet.2010.07.027
발행일
2010-10-02
유형
Article
저널명
Tetrahedron
66
40
페이지
8108 ~ 8114