Rh,
Do I have references or procedures for the alanine reaction?
Ask, and you shall recieve.
The number of examples of the Sandmeyer reaction used on amino acids is huge, and the reasons for this are pretty obvious. Amino acids are cheap chiral starting materials, and the Sandmeyer reaction allows the chemist to produce a wide array of optically pure intermediates from amino acids for asymmetric synthesis. Because this sort of thing is so ubiquitous in the literature, I've only listed examples of alpha-halo propionic acids being made from alanine, rather than include all the examples of
alpha-halogenated aliphatic acids prepared from amino acids.
Bioorganic & Medicinal Chemistry Letters (2000) 10, 17, 2037 - 2040.
Bulletin of the Chemical Society of Japan (1981) 54, 10, 3211-3212.
Bulletin of the Chemical Society of Japan (1989) 62, 8, 2562-2566.
Canadian Journal of Chemistry (1994) 72, 1, 131-141.
Chemistry Letters (1986) 1133-1136.
Farmaco (1994) 49, 9, 587-606.
Journal of Organic Chemistry (1985) 50, 9, 1356-1359.
Journal of the American Chemical Society (1954) 76, 6054,6056 Amn.20.
Journal of the American Chemical Society (1992) 114, 20, 7645-7651.
Journal of the American Chemical Society (1993) 115, 23, 11010-11011.
Journal of the Chemical Society - Perkin Transactions 1 (1987) 111-120.
Journal of the Chemical Society - Perkin Transactions 1 (1988) 3183-3194.
Journal of the Chemical Society - Perkin Transactions 1 (1998) 22, 3767-3776.
Journal of the Royal Netherlands Chemical Society (1980) 99, 3, 96-99.
Russian Chemistry Bulletin (1996) 45, 3, 676-679.
Synthesis (1987) 3, 225-228.
Tetrahedron (1995) 51, 31, 8459-8470.
Tetrahedron Letters (1985) 26, 43, 5257-5260.
Tetrahedron Letters (1987) 28, 17, 1873-1876.
Tetrahedron: Asymmetry (1993) 4, 6, 1141-1152.
There are also a great number of examples of
alpha-halo prpionic acids being made from lactic acid, and if you're interested in that, I'd be willing to submit a list of examples of that from the literature as well.
I hope this helps,
-megamole
"Give me ten minutes with your inner child, and I'll give you back an inner adult."