Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...

S. Arrasate Doktorego-Tesia
29a (1RS,2SR)-O-(N,N-diisopropilkarbamoil)-N-(p-metoxifenil)-1-(3,4-dimetoxifenil)-
2-fenil-2-aminoetanola.
OCON
H3CO Ph
H 3CO
NH
i Pr2
OCH 3
Etekina: %23.
U.p.: 69-71 o C (Et2O).
1 H-NMR (δ, ppm): 0.78 (d, J = 5.9 Hz, 6H, 2 × CH3), 0.92 (d, J = 6.3 Hz, 6H, 2 ×
CH3), 3.38-3.43 [m, 2H, 2 × CH(CH3)2], 3.75 (s, 3H, OCH3), 3.79 (s, 3H, OCH3), 3.83
(s, 3H, OCH3), 4.87 (sz, 1H NH), 5.09 (d, J = 5.9 Hz, 1H, H2), 5.37 (d, J = 5.9 Hz, 1H,
H1), 6.72-6.79 (m, 3H, Harom), 6.86-6.94 (m, 4H, Harom), 7.17-7.23 (m, 3H, Harom), 7.43-
7.47 (m, 2H, Harom).
13 C-NMR (δ, ppm): 19.2 [2 × CH(CH3)2], 21.1 [2 × CH(CH3)2], 55.3, 55.6, 55.7 (3 ×
OCH3), 71.5 (C2), 73.6 (C1), 109.9 110.5, 114.3, 119.2, 127.1, 127.4, 127.6, 129.7
(Carom-H), 134.6, 137.4, 138.2 (Carom-C, Carom-NH), 147.9, 148.6, 156.8 (Carom-O3),
160.8 (CO).
IR (CH2Cl2): 3236 (NH), 1608 (NHCOO), 1508 (NH), 1437 (CH3) cm -1 .
E.M. (IE) [m/z (ugaritasun erlatiboa)]: 341 (10), 340 (42), 297 (9), 212 (14), 149 (9),
139 (6), 129 (9), 128 (100), 91 (16), 86 (89), 58 (9).
5.5.2.2. (1RS,2RS)-28b-ren eta (1RS,2SR)-29b ren sintesia.
Prozedura orokorraren arabera, dietil eterretan disolbatutako 26b karbamatoz
(109 mg, 0.46 mmol) eta TMEDA-z (0.07 mL, 0.51 mmol) osatutako disoluzioari s-
BuLi-a gehitu zitzaion (hexanotan dagoen 0.71 M-eko disoluzio baten 0.7 mL, 0.51
196