Abstract
The reductive pinacol coupling of aldimines was studied in respect to different coupling-mediators such as mischmetall, Zn–Cu couple and Devarda alloy. High diastereoselectivity was achieved for three substrates. A simple procedure for the preparation of 1,2-diamines is described.
References
1.
Bennani Y.L.
, and
Hanessian S.
, Chem. Rev. , 1997 , 97 , 3161 .
2.
Pasini A.
, and
Zunino F.
, Angew. Chem. , 1987 , 99 , 632 .
3.
Lucet D.
,
Le Gall T.
, and
Mioskowski C.
, Angew. Chem. Int. Ed. Engl. , 1998 , 37 , 2581 .
4.
Writh T.
, Chem. Int. Ed. Engl. , 1996 , 35 , 61 .
5.
Robertson G.M.
, Comprehensive Organic Synthesis , Oxford , Pergamon Press , 1991 , vol. 3 , pp. 563 –610 .
6.
Alexakis A.
,
Aujard I.
, and
Mangeney P.
, Synlett , 1998 , 873 ; and references therein.
7.
Hatano B.
,
Ogawa A.
, and
Hirao T.
, J. Org. Chem. , 1998 , 63 , 9421 ; and references therein.
8.
Enholm E.J.
, and
Forbes D. C.
, Synth. Commun. , 1990 , 20 , 981 .
9.
Machrouchi F.
, and
Namy D. L.
, Tetrahedron Lett. , 1999 , 40 , 1315 .
10.
Helion F.
, and
Namy J. L.
, J. Org. Chem. , 1999 , 64 , 2944 .
11.
Lannou M.I.
,
Helion F.
, and
Namy J. L.
, Tetrahedron. , 2003 , 59 , 10551 .
12.
Helion F.
, and
Namy J. I.
, J. Org. Chem. , 1999 , 64 , 2944 .
13.
Shimizu M.
, and
Fujisawa T.
, Chem. Lett. , 1995 , 609 .
14.
Tsukinoi T.
, and
Mitoma Y.
, Tetrahedron Lett. , 1998 , 38 , 8873 .
15.
Simmons H.E.
, and
Smith R. D.
, Organic Synthesis , 1961 , 41 , 72 .
16.
Mäeorg U.
, and
Timotheus H.
, Proc. Acad. Sci. Estonian SSR. Chemistry (In Russian). 1985 , 34 180 –185 (CA 105:42080, 1986).
17.CRC Handbook of Chemistry and Physics. 75th edn, 1993-1995.
Lide D.
(ed.) CRC Press, Inc. Boca Ration , 1994 .
18.
Girarad P.
,
Namy J. L.
, and
Kagan B. H.
, J. Am. Chem. Soc. , 1980 , 102 , 2693 .
19.
Shimizu M.
, Tetrahedron Letters , 2001 , 42 , 8865 .
20.
Mangeney P.
,
Tejero T.
,
Alexakis A.
,
Grosjean F.
, and
Normant J.
Synthesis , 1988 , 255 .