Synthesis of optically pure threonine-containing dipeptides by regio- and stereo-controlled ring expansion of aziridine-2-imide derivatives

Abstract

The regio- and stereo-selective ring expansion of chiral N-(α-amino acyl)aziridine-2-imides to oxazolines and subsequent ring opening to optically pure threonine-containing dipeptides with the desired stereochemistry is described.

References

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12. Selected data for 5: δ_H(CDCl₃) 0.80 (d, J 6.7, 3H, CH₃CHCHPh), 1.20 (d, J 6.5, 3H, CH₃CHOAc), 1.32 (s, 9H, Bu^t), 1.95 (s, 3H, COCH₃), 2.88 (s, 3H, NCH₃), 2.95–3.18 (m, 2H, CH₂Ph), 4.00 (dq, J 6.7, 8.4, 1H, CH₃CHCHPh), 4.34–4.50 (m, 1H, CHCH₂Ph), 4.88 (d, J 6.0, 1H, HNBoc), 5.05 (d, J 8.4, 1H, CH₃CHCHPh), 5.50 (dq, J 1.3, 6.5, CHOAc), 6.08 (dd, J 1.3, 9.5, 1H, CHCHOAc), 6.65 (d, J 9.5, 1H, HNCHCH), 7.02–7.46 (m, 10H, ArH); δ_C(CDCl₃) 14.7, 20.8, 24.9, 25.6, 28.2, 33.9, 49.1, 54.3, 55.5, 59.9, 70.4, 77.8, 126.9, 128.2, 128.6, 129.2, 136.2, 136.3, 155.0, 155.4, 168.5, 170.5, 171.2.
13. J. R. Gage and D. A. Evans, Org. Synth., 1989, 68, 83.
14. Selected data for 9b: ν_max/cm^–1 3300 br, 3050, 1720, 1700, 1660; δ_H(CDCl₃) 0.93 (d, J 6.0, CH₃), 1.35 (s, 9H, Bu^t), 2.85–3.20 (m, 2H, CH₂Ph), 4.20–4.40 (m, 1H, CHOH), 4.40–4.67 (m, 2H, CHCHOH + CHCH₂Ph), 5.40 (d, J 6.0, 1H, HNBoc), 6.00–6.40 (m, 3H, OH +HNCHCH + CO₂H), 7.10–7.40 (m, 5H, ArH); δ_C(CDCl₃) 19.3, 28.2, 38.9, 55.7, 57.4, 67.6, 80.1, 127.0, 128.6, 129.3, 136.4, 156.3, 172.2, 173.4; [α]_D–11.4 (c 4, CHCl₃).
15. Selected data for 10b: ν_max/cm^–1 3350, 3050, 1750, 1694, 1659, 1525; δ_H(CDCl₃) 1.00 (d, J 6.1, 3H, CH₃), 1.32 (s, 9H, But), 2.95 (dd, J 6.7, 13.9, 1H, CH₂Ph), 3.11 (dd, J 6.2, 13.9, 1H, CH₂Ph), 3.67 (s, 3H, CO₂CH₃), 4.20–4.32 (m, 1H, CHOH), 4.40–4.60 (m, 2H, CHCHOH + CHCH₂Ph), 5.40–5.58 (br s, 1H, HNBoc), 7.10–7.33 (m, 6H, ArH +HNCHCH); δ_C(CDCl₃) 19.5, 28.0, 33.6, 38.3, 52.2, 57.5, 67.2, 79.8, 126.5, 128.2, 129.1, 136.5 155.2, 171.2, 172.2; [α]_D–7.7 (c 5, CHCl₃).