Abstract
Both enantiomers of amphetamine hydrochloride were stereospecifically synthesised based on bakers’ yeast reduction of phenylacetone. A simple and efficient method for the chiral inversion of (S)-1-phenyl-2-propanol
References
1.
(a)
Pelletier S. W.
, Chemistry of Alkaloids , Van Nostrand-Reinhold : New York , 1970 .
2.
Leake C. D.
, The Amphetamines: Their Actions and Uses , Charles C. Thomas Co. : Springfield , 1958 .
3.
Testa B.
,
Salvesen B.
, J. Pharm. Sci. , 1980 , 69 , 497 .
4.
(a)
Brussee J.
,
Jansen A. C. A.
, Tetrahedron Lett. , 1983 , 24 , 3261 .
5.
Brussee J.
,
Groenendijk J. L. G.
,
Koppele J. M.
,
Jansen A. C. A.
, Tetrahedron , 1985 , 41 , 3313 .
6.
(a)
Mori A.
,
Ishiyama I.
,
Akita H.
,
Suzuki K.
,
Mitsuoka T.
,
Oishi T.
, Chem. Pharm. Bull. , 1990 , 38 , 3449 .
7.
Krasik P.
,
Alper H.
, Tetrahedron: Asymmetry , 1992 , 3 , 1283 .
8.
Bell F.W.
,
Cantrell A. S.
,
Hoegberg M.
,
Jaskunas S. R.
,
Johansson N. G.
, J. Med. Chem. , 1995 , 25 , 4929 .
9.
Micovic I.V.
,
Ivanovic M. D.
,
Roglic G. M.
,
Kiricojevic V. D.
,
Popovic J. B.
, J. Chem. Soc. Perkin Trans. 1 , 1996 , 265 .
10.
Kabalka G.W.
,
Guindi L. H. M.
,
Varma R. S.
, Tetrahedron , 1990 , 46 , 7443 .
11.
Fuji M.
, Chem. Lett. , 1992 , 6 , 933 .
12.
Hartung C.G.
,
Breindl C.
,
Tillack A.
,
Beller M.
, Tetrahedron , 2000 , 56 , 5157 .
13.
(a)
Nicols D.E.
,
Barfknecht C. F.
,
Rusterholz D. B.
, J. Med. Chem. , 1973 , 16 , 480 .
14.
Rozwadowska M.D.
, Tetrahedron: Asymmetry , 1993 , 4 , 1619 .
15.
Wagner J.M.
,
McElhinny C. J.
Jr.
,
Lewin A. H.
,
Carroll F. I.
, Tetrahedron: Asymmetry , 2003 , 14 , 2119 .
16.
(a)
Roberts S.M.
, J. Chem. Soc. Perkin Trans. 1 , 1999 , 1 .
17.
Roberts S. M.
, J. Chem. Soc. Perkin Trans. 1 , 2000 , 611 .
18.
(a)
Nakamura K.
,
Matsuda T.
,
Ohno A.
, Tetrahedron: Asymmetry , 1996 , 7 , 3021 .
19.
Gillois J.
,
Jaouen G.
,
Buisson D.
,
Azerad R.
, J. Organomet. Chem. , 1989 , 367 , 85 .
20.
(a)
Mitsunobu O.
, Synthesis , 1981 , 1 .
21.
Castro B.R.
, Org. React. , 1983 , 29 , 1 .
22.
Hughes D.L.
, Org. React. , 1992 , 42 , 335 .
23.
Larock R.C.
, Comprehensive Organic Transformations , 2nd edn., VCH Publishing Inc. : New York , 1999 , p. 965 .
