Helvetica Chimica Acta p. 1852 - 1861 (2003)
Update date:2022-09-26
Topics:
Seebach, Dieter
Schaeffer, Laurent
Gessier, Francois
Bindschaedler, Pascal
Jaeger, Corinna
Josien, Delphine
Kopp, Sascha
Lelais, Gerald
Mahajan, Yogesh R.
Micuch, Peter
Sebesta, Radovan
Schweizer, Bernd W.
Multigram amounts of suitably protected β2-amino acids with 17 of the 20 proteinogenic side chains are prepared by diastereoselective reactions of Li, B, or Ti enolates of the corresponding 3-acyl-4-isopropyl-5,5-diphenyloxazolidin-2-ones (acyl-DIOZ; 1) with appropriate electrophiles (amidomethylation, hydroxyalkylation, (benzyloxycarbonyl)methylation) in yields of 55-90% and with diastereoselectivities of 80 to > 97% (Scheme). The primary products 2-8 thus obtained are converted to protected β2-amino acids by standard procedures (Table 1). Many of the DIOZ derivatives are highly crystalline compounds (31 X-ray crystal structures in Table 2). The chiral auxiliary DIOZ, readily prepared in either enantiomeric form, is recovered with high yield.
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