A. Carloni et al. / Tetrahedron: Asymmetry 9 (1998) 2987–2998
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4.14. (3R,6S,10S)-3,6-Diallyl-3,6-dimethyl-4-N-(10 -phenethyl)-1,4-morpholin-2,5-dione 6c
Allyl iodide was used as the alkylating reagent. The reaction occurred over 4 h and the pure product
1
was isolated in 79% yield. H-NMR δ 1.63 (s, 3H), 1.72 (s, 3H), 1.95 (d, 3H, J=7 Hz), 2.41 (dd, 1H,
J=7.5, 13.8 Hz), 2.75 (dd, 1H, J=7.2, 13.8 Hz), 2.78 (m, 2H), 4.52 (q, 1H, J=7 Hz), 5.1 (m, 2H), 5.3 (m,
2H), 5.6 (m, 1H), 5.8 (m, 1H), 7.35 (m, 5ArH); 13C-NMR δ 18.5, 25.6, 26.2, 42.9, 44.4, 54.2, 66.0, 82.5,
116.6, 120.2, 125.9, 126.3, 127.3, 130.6, 131.3, 141.1, 165.8, 167.8. [α]D=−52.0 (c=1.4, CHCl3). Anal.
calcd for C20H25NO3: C, 73.37; H, 7.7; N, 4.28. Found: C, 73.29; H, 7.68; N, 4.3.
4.15. (3S,6S,10S)-3,6-Diallyl-3,6-dimethyl-4-N-(10 -phenethyl)-1,4-morpholin-2,5-dione 7c
The product was isolated in 16% yield. 1H-NMR δ 1.62 (s, 3H), 1.8 (s, 3H), 1.91 (d, 3H, J=6.8 Hz),
2.51 (dd, 1H, J=7.1, 14.6 Hz), 2.73 (m, 2H), 2.87 (dd, 1H, J=7.4, 14.6 Hz), 4.54 (q, 1H, J=6.8 Hz), 4.94
(m, 2H), 5.18 (m, 2H), 5.42 (m, 1H), 5.76 (m, 1H), 7.35 (m, 5ArH); 13C-NMR δ 20.9, 26.5, 27.2, 43.3,
44.1, 56.7, 66.8, 83.5, 120.5, 120.8, 127.1, 127.7, 128.1, 131.3, 140.6, 167.1, 168.0.
4.16. (3R,6S,10S)-6-Allyl-3-ethyl-3,6-dimethyl-4-N-(10 -phenethyl)-1,4-morpholin-2,5-dione 6d
Ethyl iodide was used as the alkylating reagent. The reaction occurred over 8 h and the pure product
was isolated in 74% yield. 1H-NMR δ 1.02 (t, 3H, J=7.2 Hz), 1.62 (s, 3H), 1.75 (s, 3H), 1.87 (d, 3H, J=7
Hz), 2.03 (m, 2H), 2.47 (dd, 1H, J=7.5, 13.7 Hz), 2.69 (dd, 1H, J=7.2, 13.7 Hz), 4.45 (q, 1H, J=7 Hz),
5.05 (m, 2H), 5.50 (m, 1H), 7.32 (m, 5ArH); 13C-NMR δ 9.1, 20.8, 26.4, 27.1, 32.2, 43.7, 56.3, 66.9,
82.9, 120.2, 126.9, 127.4, 127.6, 127.9, 131.0, 141.2, 167.3, 169.3. [α]D=−48.7 (c=1.2, CHCl3). Anal.
calcd for C19H25NO3: C, 72.35; H, 7.99; N, 4.44. Found: C, 72.64; H, 7.97; N, 4.43.
4.17. (3S,6S,10S)-6-Allyl-3-ethyl-3,6-dimethyl-4-N-(10 -phenethyl)-1,4-morpholin-2,5-dione 7d
The product was isolated in 16% yield. 1H-NMR δ 0.63 (t, 3H, J=7.3 Hz), 1.63 (s, 3H), 1.77 (s, 3H),
1.87 (d, 3H, J=7 Hz), 1.83–2.15 (m, 2H), 2.49 (dd, 1H, J=7.3, 14 Hz), 2.89 (dd, 1H, J=7.1, 13.8 Hz),
4.43 (q, 1H, J=7 Hz), 5.2 (m, 2H), 5.75 (m, 1H), 7.35 (m, 5ArH); 13C-NMR δ 9.2, 18.7, 26.8, 27.1, 32.8,
45.3, 54.8, 66.7, 83.1, 121.2, 126.7, 127.0, 127.7, 130.4, 140.7, 166.6, 168.9.
4.18. (3R,6S,10S)-3,6-Dibenzyl-3,6-dimethyl-4-N-(10 -phenethyl)-1,4-morpholin-2,5-dione 6e
Benzyl bromide was used as the alkylating reagent. The reaction occurred over 5 h and the pure product
was obtained in 85% yield. 1H-NMR δ 1.0 (s, 3H), 1.06 (s, 3H), 1.93 (d, 3H, J=7 Hz), 2.85 (d, 1H, J=13.7
Hz), 3.2 (qAB, 2H, J=14.3 Hz), 3.25 (d, 1H, J=13.7 Hz), 4.49 (q, 1H, J=7 Hz), 7.24 (m, 15ArH); 13C-NMR
δ 21.7, 26.8, 27.1, 45.1, 46.5, 56.4, 67.9, 84.2, 126.8, 126.9, 127.6, 127.7, 127.9, 128.1, 128.4, 130.3,
131.0, 134.3, 134.4, 141.4, 166.5, 168.1. [α]D=−50.2 (c=1.1, CHCl3). Anal. calcd for C28H29NO3: C,
78.66; H, 6.84; N, 3.28. Found: C, 78.45; H, 6.87; N, 3.27.
4.19. (3S,6S,10S)-3,6-Dibenzyl-3,6-dimethyl-4-N-(10 -phenethyl)-1,4-morpholin-2,5-dione 7e
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The pure product was isolated in 9% yield. H-NMR δ 1.60 (s, 3H), 1.80 (s, 3H), 1.90 (d, 3H, J=7
Hz), 2.59 (d, 1H, J=14.2 Hz), 2.59 (d, 1H, J=14.1 Hz), 2.85 (qAB, 2H, J=13.8 Hz), 3.18 (d, 1H, J=14.1
Hz), 4.63 (q, 1H, J=7 Hz), 6.72 (m, 2H), 7.17 (m, 13ArH); 13C-NMR δ 19.8, 26.0, 27.5, 45.0, 45.2, 56.2,