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Synthesis 2001(5): 0693-0695
DOI: 10.1055/s-2001-12768
DOI: 10.1055/s-2001-12768
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Practical One-Step Synthesis of Koga’s Chiral Bases
Further Information
Received
13 September 2000
Publication Date:
15 October 2004 (online)
Publication History
Publication Date:
15 October 2004 (online)
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Abstract
A simple, efficient and practical method for the preparation of Koga"s chiral bases is described. The method involves attack of an amine on a styrene oxide-derived aziridinium ion and has allowed the synthesis of novel diamines which cannot be prepared using Koga"s original route.
Key words
amines - chirality - amino alcohols - aziridinium ions
- 1 For a review, see:
O"Brien P. J. Chem. Soc., Perkin Trans. 1 1998, 1439 - For recent examples, see:
-
2a
Majewski M.Ulaczyk A.Wang F. Tetrahedron Lett. 1999, 40: 8755 -
2b
de Sousa SE.O"Brien P.Steffens HC. Tetrahedron Lett. 1999, 40: 8423 -
2c
Aggarwal VK.Humphries PS.Fenwick A. Angew. Chem. Int. Ed. 1999, 38: 1985 -
2d
Asami M.Ogawa M.Inoue S. Tetrahedron Lett. 1999, 40: 1563 -
2e
Södergen MJ.Andersson PG. J. Am. Chem. Soc. 1998, 120: 10760 -
2f
Södergen MJ.Bertilsson SK.Andersson PG. J. Am. Chem. Soc. 2000, 122: 6610 -
2g
Clayden J.Johnson P.Penk JH. J. Chem. Soc., Perkin Trans 1 2001, 371 - 3
Cain CM.Cousins RPC.Coumbarides G.Simpkins NS. Tetrahedron 1990, 46: 523 -
4a
Shirai R.Tanaka M.Koga K. J. Am. Chem. Soc. 1986, 108: 543 -
4b
Shirai R.Sato D.Aoki K.Tanaka M.Kawasaki H.Koga K. Tetrahedron 1997, 53: 5963 - 5
Shirai R.Aoki K.Sato D.Kim HD.Murakata M.Yasukata T.Koga K. Chem. Pharm. Bull. 1994, 42: 690 -
6a
Smith AB.Nolen EG.Shirai R.Blase FR.Ohta M.Chida N.Hartz RA.Fitch DM.Clark WM.Sprengler PA. J. Org. Chem. 1995, 60: 7837 -
6b
MaGee DI.Setiadji S.Martin RA. Tetrahedron: Asymmetry 1995, 6: 639 -
6c
Momose T.Toshima M.Seki S.Koike Y.Toyooka N.Hirai Y. J. Chem. Soc., Perkin Trans. 1 1997, 1315 -
6d
Majewski M.Lazny R. Tetrahedron Lett. 1994, 35: 3653 - 7
Saravanan P.Singh VK. Tetrahedron Lett. 1998, 39: 167 - 8
de Sousa SE.O"Brien P.Poumellec P. J. Chem. Soc., Perkin Trans. 1 1998, 1483 - 10
Meister W.Guthrie RD.Maxwell JL.Jaeger DA.Cram DJ. J. Am. Chem. Soc. 1969, 91: 4452 - 11
Murakata M.Nakajima M.Koga K. J. Chem. Soc., Chem. Commun. 1990, 1657 - 12
Jain ASG.Huang SG.Whitesides GM. J. Am. Chem. Soc. 1994, 116: 5057 - 13
Yamishita Y.Odashima K.Koga K. Tetrahedron Lett. 1999, 40: 2803 - 14
Yamashita Y.Emura Y.Odashima K.Koga K. Tetrahedron Lett. 2000, 41: 209
References
The enantiomeric excess of diamine (R)-2 was established as 95% ee using 1H NMR spectroscopy in the presence of a chiral shift reagent, (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol.