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Synthesis 2006(7): 1093-1098
DOI: 10.1055/s-2006-926389
DOI: 10.1055/s-2006-926389
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of New Chiral Mixed cis-Tetraheterodecalines by Highly Selective Cyclization of N,N′-Bisalkyl 2,3-Diaminobutanediols
Further Information
Received
10 October 2005
Publication Date:
08 March 2006 (online)
Publication History
Publication Date:
08 March 2006 (online)
![](https://www.thieme-connect.de/media/synthesis/200607/lookinside/thumbnails/10.1055-s-2006-926389-1.jpg)
Abstract
Chiral secondary vic-diamines of diaminobutanediols have been efficiently prepared from l-tartaric acid. Their selective cyclization led to cis-tetraheterodecalines having a (1S,6S)-2,7-diaza-4,9-dioxa[4.4.0]decane core system.
Key words
amino alcohols - fused-ring systems - heterocycles - ring closure
- 1
Lucet D.Le Gall T.Mioskowski C. Angew. Chem. Int. Ed. 1998, 37: 2580 - Reviews for C 2 -symmetric ligands:
-
2a
Whitesell JK. Chem. Rev. 1989, 89: 1581 -
2b
Ghosh AK.Mathivanan P.Cappiello J. Tetrahedron: Asymmetry 1998, 9: 1 - 3
Hirama M.Oishi T.Itô S. J. Chem. Soc., Chem. Commun. 1989, 665 - 4
Helmchen G.Krotz A.Ganz K.-T.Hansen D. Synlett 1991, 257 - 5
Evans DA.Woerpel KA.Hinman MM.Faul MM. J. Am. Chem. Soc. 1991, 113: 726 - 6
Muller D.Umbricht G.Pfaltz A. Helv. Chim. Acta 1991, 74: 232 -
7a
Feit PW.Nielsen OT. J. Med. Chem. 1967, 10: 697 -
7b
Feit PW.Nielsen OT. J. Med. Chem. 1970, 13: 447 -
7c
Haines AH.Morley C.Murrer BA. J. Med. Chem. 1989, 32: 742 -
7d
Hanessian S.Gauthier J.-Y.Okamoto K.Beauchamp AL.Theophanides T. Can. J. Chem. 1993, 71: 880 - 8
Lee S.-g.Lim CW.Song CE.Okim I.Jun C.-H. Tetrahedron: Asymmetry 1997, 8: 2927 - 9
Tanner D.Railton CJ.Pettersson I.Sotofte I. Acta Chem. Scand. 1999, 53: 703 - 10
Lee S.-g.Lim CW.Song CE.Kim KM.Jun C.-H. J. Org. Chem. 1999, 64: 4445 -
11a
Gras J.-L.Pellisier H.Nouguier R. J. Org. Chem. 1989, 54: 5675 -
11b
Gras J.-L.Pellisier H. Tetrahedron 1991, 32: 7043 -
11c
Gras J.-L.Dulphy H.Lejon T. Tetrahedron 1996, 52: 8517 -
11d
Gras J.-L.Soto T.Viala J. Tetrahedron: Asymmetry 1997, 8: 3829 - 12
Gras J.-L.Dulphy H.Lejon T. Bull. Soc. Chim. Fr. 1994, 131: 418 - 13
Hoppe D.Hintze F.Tebben P. Angew. Chem., Int. Ed. Engl. 1990, 29: 1422 - 14
Li X.Schenkel LB.Kozlowski MC. Org. Lett. 2000, 2: 875 - 15
Star A.Lemcoff G.Goldberg I.Fuchs B. Tetrahedron Lett. 1997, 38: 3573 - 16
Oishi T.Hirama M. Tetrahedron Lett. 1992, 33: 639 - 17
Scheuren A.Mosset P.Saalfranck RW. Tetrahedron: Asymmetry 1999, 10: 3559 - 18
Star A.Lemcoff G.Goldberg I.Lemcoff NG.Fuchs B. Eur. J. Org. Chem. 1999, 2033 - 19
Roberts JJ.Ross WC. J. Chem. Soc. 1952, 4288 - 20
Agami C.Rizk T. Tetrahedron 1985, 41: 537 - 21
Riddell FG.Lehn J.-M. J. Chem. Soc., B 1968, 1224 - 22
Perrin DD.Armengo WLF. Purification of Laboratory Chemicals 3rd ed.: Pergamon; Oxford: 1988.