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to afford pure 2a (R1=CH2CHꢀCH2) (2.3 g, 85%): an
oil; [h]D +9.6 (c 1, CHCl3); IR (film) 2100, 1730, 1710,
1
1630 cm−1; H NMR (CDCl3): l 7.36–7.28 (5H, aromat-
ics-H), 5.87 (1H, m, CH2ꢀCH-CH2), 5.52 (1H, d, J=5.8
Hz, NH), 5.30 (1H, d, J=17.2 Hz, CHHꢀCH-CH2), 5.23
(1H, d, J=10.5 Hz, CHHꢀCH-CH2), 5.20 (1H, bs, 6-H),
5.11–5.05 (2H, AB system, OCH2Ph), 4.60 (2H, d, J=4.1,
CH2ꢀCH-CH2), 4.36 (1H, m, 2-H), 2.43–2.32 (2H, over-
lapping, 4-Ha and 4-Hb), 2.20 (1H, m, 3-Ha), 1.99 (1H,
m, 3-Hb). Anal. calcd for C17H19N3O5: C, 59.12; H, 5.55;
N, 12.17. Found: C, 59.37; H, 5.41; N, 12.31%.
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20. Compounds 2b–g, after hydrogenolysis (H2, Pd/C,
14. All new compounds show correct elemental analyses and
consistent physicochemical properties.
15. The allyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxo-
hexanoate 2a (R%=CH2CHꢀCH2) was prepared by treat-
ment of (S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobut-
yl)-5-oxazolidinone 1a (2.5 g, 7.9 mmol) with NaHCO3
(1.5 g) and allylic alcohol (75 mL; to obtain the methyl or
ethyl esters, 200 mL of the appropriate alcohols were
used) at reflux for 10 min. The solvent was then evapo-
rated under reduced pressure and the residue oil was
chromatographed (eluting with hexane:AcOEt, 60:40 v/v)
MeOH,
rt,
12
h),
were
trifluoroacetylated
[(CF3CO)2:CF3CO2H; 1:1, v/v, rt, 2 h)] and their behav-
ior on chiral GLC13,21 [octakis(3-O-butyryl-2,6-di-O-pent-
yl)-g-cyclodextrin (Lipodex E) capillary column] was
examined and compared with that of the corresponding
derivatives of natural and racemic amino acids, prepared
as described by us for hydroxylysine.13
21. Koning, W. A. J. High Resolut. Chromatogr. 1993, 16,
569–586.
.