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
References
1 O"Brien P.
J. Chem. Soc., Perkin Trans. 1
1998,
1439
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
9 The enantiomeric excess of diamine (R )-2 was established as 95% ee using 1 H NMR spectroscopy in the presence of a chiral shift reagent, (R )-2,2,2-trifluoro-1-(9-anthryl)ethanol.
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
