Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2004(1): 122-124
DOI: 10.1055/s-2003-43353
DOI: 10.1055/s-2003-43353
LETTER
© Georg Thieme Verlag Stuttgart · New York
Diastereopure Preparation of α-Benzotriazolyl 1-Azacycloalka[2,1-b][1,3]-oxazines and their Application as Versatile Chiral Precursors
Further Information
Received
3 October 2003
Publication Date:
26 November 2003 (online)
Publication History
Publication Date:
26 November 2003 (online)
Abstract
A group of diastereopure α-benzotriazolyl 1-azacycloalka[2,1-b][1,3]oxazines were prepared from non-racemic Betti base and they were employed as the versatile precursors for the preparation of chiral ligands and chiral substituted azacyclics with significant advantages in the stereoselectivity.
Key words
Betti base - chiral [1,3]oxazines - chiral ligands - chiral substituted azacyclics
- For reviews, see:
-
1a
Soai K.Niwa S. Chem. Rev. 1992, 92: 833 -
1b
Ager DJ.Prakash I.Schaad DR. Chem. Rev. 1996, 96: 835 -
1c
Pu L.Yu HB. Chem. Rev. 2001, 101: 757 -
2a
Husson H.-P.Royer J. Chem. Soc. Rev. 1999, 28: 383 -
2b
Gauthier I.Royer J.Husson H.-P. J. Org. Chem. 1997, 62: 6704 -
2c
Francois D.Poupon E.Lallemand M.-C.Kunesch N.Husson H.-P. J. Org. Chem. 2000, 65: 3209 -
2d
Blanchet J.Bonin M.Nicouin L.Husson H.-P. J. Org. Chem. 2000, 65: 6423 -
2e
Poupon E.Luong B.-X.Chiaroni A.Kunesch N.Husson H.-P. J. Org. Chem. 2000, 65: 7208 -
2f
Cutri S.Micouin L.Husson H.-P.Chiaroi A. J. Org. Chem. 2003, 68: 2645 -
3a
Katritzky AR. J. Heterocycl. Chem. 1999, 36: 1501 -
3b
Katritzky AR.Qiu G.Yang B.Steel PJ. J. Org. Chem. 1998, 63: 6699 -
3c
Kartritzky AR.Cui X.-L.Yang B.Steel PJ. J. Org. Chem. 1999, 64: 1979 -
4a
Meyers AI.Snyder L. J. Org. Chem. 1992, 57: 3814 -
4b
Meyers AI.Snyder L. J. Org. Chem. 1993, 58: 36 -
4c
Munchof MJ.Meyers AI. J. Org. Chem. 1995, 60: 3189 -
4d
Munchof MJ.Meyers AI. J. Org. Chem. 1995, 60: 7084 -
4e
Munchof MJ.Meyers AI. J. Org. Chem. 1995, 60: 7086 -
4f
Munchof MJ.Meyers AI. J. Org. Chem. 1996, 61: 4607 -
4g
Kamata K.Agata I.Meyers AI. J. Org. Chem. 1998, 63: 3113 -
4h
Meyers AI.Downing SV.Weiser MJ. J. Org. Chem. 2001, 66: 1413 -
5a
Yamazaki N.Ito T.Kibayashi C. Tetrahedron. Lett. 1999, 40: 739 -
5b
Yamazaki N.Ito T.Kibayashi C. Org. Lett. 2000, 2: 465 -
5c
Yamazaki N.Dokoshi W.Kibayashi C. Org. Lett. 2001, 3: 193 -
5d
Ito T.Yamazaki N.Kibayashi C. Org. Lett. 2002, 4: 2469 -
6a
Cardelliccnio C.Ciccarella G.Naso F.Schingaro E.Scordari F. Tetrahedron: Asymmetry 1998, 9: 3667 -
6b
Cardelliccnio C.Ciccarella G.Naso F.Perna F.Tortorella P. Tetrahedron 1999, 55: 14685 -
6c
Bernardinelli G.Fernandez D.Gosmini R.Meier P.Ripa A.Schupfer P.Treptow B.Kundig EP. Chirality 2000, 12: 529 -
6d
Palmieri G. Tetrahedron: Asymmetry 2000, 11: 3361 -
6e
Liu D.-X.Zhang L.-C.Wang Q.Da CS.Xin Z.-Q.Wang R.Choi MCK.Chan ASC. Org. Lett. 2001, 3: 2733 -
6f
Cimarelli C.Mazzanti A.Palmieri G.Volpini E. J. Org. Chem. 2001, 66: 4759 -
6g
Wang Y.Li X.Ding K. Tetrahedron: Asymmetry 2002, 13: 1291 -
6h
Ji J.Qiu L.Yip CW.Chan ASC. J. Org. Chem. 2003, 68: 1589 -
7a
Lu J.Xu X.Wang C.He J.Hu Y.Hu H. Tetrahedron Lett. 2002, 43: 8367 -
7b
Lu J.Xu X.Wang S.Wang C.Hu Y.Hu H. J. Chem. Soc., Perkin Trans. 1 2002, 2900