Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...

S. Arrasate Doktorego-Tesia
1 H-NMR (δ, ppm): 0.76 (d, J = 6.7 Hz, 6H, 2 × CH3), 1.11 (d, J = 6.7 Hz, 6H, 2 ×
CH3), 3.56-3.68 [m, 2H, 2 × CH(CH3)2], 3.71 (s, 3H, OCH3), 3.72 (s, 3H, OCH3), 3.73
(s, 3H, OCH3), 5.09 y 5.21 (sistema AB, J = 12.1 Hz, 2H, CH2Ph), 5.72 (d, J = 11.5 Hz,
1H, H2), 6.26 (d, J = 11.5 Hz, 1H, H1), 6.59-6.69 (m, 3H, Harom), 6.75-6.79 (m, 2H,
H ), 6.96-6.99 (m, 5H, NCOOCH2Ph), 7.29-7.36 (m, 7H, C2-Ph, 2 × CHarom-CN).
arom
13 C-NMR (δ, ppm): 19.5 [2 × CH(CH3)2], 21.4 [2 × CH(CH3)2], 55.2, 55.5, 55.7 (3 ×
OCH3), 65.1 (C2), 69.5 (CH2Ph), 80.2 (C1), 110.2 110.6, 113.9 (4 × Carom-H),
120.9(CaromH-CaromCHO), 126.8, 127.3, 127.4, 128.3, 128.4, 129.6, 129.7, 129.9 (10 ×
Carom-H, CaromN, 2 × Carom-H), 135.2, 136.1, 136.3 (Carom-C1, Carom-O, CaromCH2), 148.3,
148.6, (Carom-O, Carom-C2), 154.7 (Carom-O), 157.3 (NCOOCH2Ph), 161.6 (OCON i Pr2).
IR (CH2Cl2): 2919 (CH3), 2849 (OCH2), 1637 (C=O), 1508 (N-C=O) cm -1 .
E.M. (IE) [m/z (ugaritasun erlatiboa)]: 339 (11), 240 (5), 233 (5), 211 (7), 196 (6), 165
(6), 149 (5), 129 (12), 128 (87), 108 (11), 97 (10), 91 (39), 87 (11), 86 (100), 85 (28), 83
(38), 79 (17), 77 (15), 73 (13), 71 (20), 70 (11), 69 (20), 60 (13), 57 (40), 56 (11), 55
(32), 51 (9).
5.6. N-FENETILSUKZINIMIDEN ERREAKTIBO ORGANOLITIKOEN ADIZIO
NUKLEOZALEA−N-AZILIMINIO IOIEN BIDEZKO ZIKLAZIOA ETA
METALAZIOA−PARHAM ZIKLAZIOA.
5.6.1. 43 (S)-(−)-N-[1-(t-butildifenilsililoxi)-3-(3,4-dimetoxifenil)-prop-2-
il]sukzinimidaren sintesi enantioselektiboa.
5.6.1.1. 38 Metil (S)-(+)-(t-butoxikarbonilamino)-3-(3,4-dimetoxifenil)propanoatoren
sintesia.
%50 Dioxano/uretan (80 mL) dagoen 36 L-DOPA-ren [3-(3,4-dimetoxifenil)-L-
alanina] (5 g, 25.35 mmol) disoluzioari NEt3 (4.24 mL, 30.4 mmol) gehitu zitzaion.
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