US EPA

1494761 

Journal Article 

Enantiospecific alkylations of alanine 

Alonso, F; Davies, SG; Elend, AS; Haggitt, JL 

1998 

Journal of the Chemical Society, Perkin Transactions 1
ISSN: 1472-7781
EISSN: 1364-5463 

2 

257-264 

English 

10.1039/a705764d 

WOS:000071773900014 

http://://WOS:000071773900014
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Reaction of ferrocenecarbaldehyde 3 with sodium (S) alaninate followed by pivaloyl chloride generates (2S,4S)-2-ferrocenyl-3-pivaloyl-4-methyl-1,3 oxazolidin-5-one 5 (>98% de), Compound 5 undergoes stereospecific 4-alkylation with complete
retention of configuration on treatment sequentially with lithium diisopropylamide and an
appropriate alkyl bromide (benzyl bromide, allyl bromide, crotyl [(E)-but-2-enyl] bromide,
alpha-bromo-o-xylene, cinnamyl bromide, 2-(bromomethyl)naphthalene, 1-(tert-butoxycarbonyl)-3-
(bromomethyl)indole and bromoacetonitrile} to generate the corresponding (2S,4R)-2-ferrocenyl-3-
pivaloyl-4-alkyl-4-methyl-1,3-oxazolidin-5-ones 7a-h. Hydrolysis of (2S,4R)-7a-h on Amberlyst-15
generates the free (R)-alpha-methyl-alpha-amino acids (R)-8a-h.