Helvetica Chimica Acta p. 1243 - 1250 (1985)
Update date:2022-08-04
Topics:
Seebach, Dieter
Fadel, Antoine
The sodium salt of (S)-alanine, (S)-phenylalanine, (S)-valine, and (S)-methionine are condensed with pivalaldehyde to imines 5.Cyclization by treatment with benzoyl chloride in cold CH2Cl2 gives mainly (4:1 to > 99:1) the (2S,4S)-4-alkyl-3-benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones (6; cis-configuration) in high yields (85-95 percent).The oxazolidinones 6 and 7 are deprotonated with lithium diethylamide (LDEA) in tetrahydrofuran (THF) and alkylated (MeI, benzyl bromide) or hydroxyalkylated (benzaldehyde) to 4,4-disubstituted oxazolidinones 9 and 10, respectively, with high diastereoselectivity (9:1 to 50:1; relative topicity ul).Hydrolysis of three of the oxazolidinones to amino acids of known configuration and optical purity indicates that little if any racemization occurs in the process.
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(1985)Doi:10.1002/hlca.193702001158
(1937)Doi:10.1016/j.tet.2008.04.107
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(2016)