Adamantyl amines were prepared by samarium-metal induced iodine-catalysed reduction of the imines in a one-pot operation.
References
1.
For some recent references, see: (a) MainB.G., and TuckerH. In Medicinal Chemistry, 2nd edn.; C.R. Genellin and S.M. Roberts, New York: Academic Press, 1983, 187
2.
AskinD., WallaceM. A., VaccaJ. P., ReamerR. A., VolanteR. P., and ShinkaiI.J. Org. Chem., 1992, 57, 2771
3.
ManchandP.S., CerrutiR. L., MartinJ. A., HillC. H., MerrettJ. H., KeechE., BelsheR. B., ConnelE. V., and SimI. S.J. Med. Chem., 1990, 33, 1992
HutchinsR.O., and NataleN.Org. Prep. Proced. Int., 1979, 11, 201
8.
LaneC.F., Synthesis1975, 135.
9.
(a) BorchR.F., BernsteinM. D., and DurstH. D., J. Am. Chem. Soc., 1971, 93, 2897
10.
BorchR.F.Org. Synth., Coll.6, 1988, 499
11.
Abdel-MagidA.F., MaryanhoffC. A., and CarsonK. G.Tetrahedron Lett., 1990, 31, 5595
12.
VeradoG., GiumaniniA. G., StrazzoliniP., and PoianaM., Synthesis1993, 121.
13.
Bhattacharyya has carried out elegant study on the reductive amination by titanium isopropoxide. For example, see: (a) BhattacharyyaS., J. Org. Chem., 1995, 60, 4928
14.
BhattacharyyaS., J. Chem. Res. (S) 1995, 36
15.
BhattacharyyaS.; Synth. Commun.1995, 25, 2061
16.
BhattacharyyaS., ChatterjeeA., and DuttachowdhuryS. K., J. Chem. Soc. Perkin Trans. 1, 1994, 1.
BanikB.K., ZegrockaO., BanikI., HackfeldL., and BeckerF. F.Tetrahedron Lett., 1999, 40, 6731. Also see: A. Ghatak, F.F. Becker, B.K. Banik, Tetrahedron Lett. 2000, 41, 3793. For an elegant study of the use of samarium metal in organic synthesis, see: R. Yanada, N. Negoro, M. Okaniwa and T. Ibuka Tetrahedron, 1999, 55, 13947 and references cited therein.
22.
For some examples of one-pot synthetic methods, see: (a) MinutiL., TaticchiA., Gacs-BaitzE., MarrocchiA., Tetrahedron, 1998, 54, 10891
23.
OguzU., AkkayaE. U., J. Org. Chem., 1998, 63, 6059
24.
BanikB.K., ManhasM. S., RobbE. W., BoseA. K., Heterocycles, 1997, 44, 405