Asymmetric α -Amination of chiral protected -hydroxyaldehydes catalyzed by proline

Synlett

Volumn , Issue 18, 2009, Pages 3007-3010

  Ait Youcef, Ramzi ^a   Sbargoud, Kamal ^a   Moreau, Xavier ^a   Greck, Christine ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

2 hydrazino 1,3 diol; Amination; Azodicarboxylate; Diastereoselectivity; Hydroxyaldehyde; Organocatalysis

Indexed keywords

HYDROXYALDEHYDE; PROLINE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY;

EID: 72049110524     PISSN: 09365214     EISSN: 14372096     Source Type: None    
DOI: 10.1055/s-0029-1218001     Document Type: Article

References (26)

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24. 3-tert-Butyldimethylsilyloxybutanal (1) was synthesized in two steps (TBS protection and DIBAL-H reduction of the ester moiety) from ethyl 3-hydroxybutyrate commercially available in both enantiomeric forms.
25. General Procedure for the Organocatalytic a-Amination: Dibenzylazodicarboxylate (1 mmol) and D- L-proline (0.2 mmol, 20 mol%) in MeCN (10 mL) were treated with an aldehyde (1.5 mmol) at r.t. The reaction mixture was stirred at this temperature until the yellow color of the azodicarboxylate had disappeared. The mixture was treated with EtOH (10 mL) and NaBH4 (40 mg) and was stirred for 5 min at 0 °C. The reaction was worked up with aq NH4Cl solution and EtOAc. The organic layers were dried (MgSO4), filtered, and concentrated. Medium-pressure column chromatography on silica gel with EtOAc-pentane mixture (1:4) gave the desired anti- or syn-2-hydrazino-1,3- diol as a single diastereomer.
26. Characterization of Selected Compounds: Compound 2: 1H NMR (300 MHz, CDCl3): d = 0.01-0.05 (m, 6 H), 0.86 (s, 9 H), 1.08-1.16 (m, 3 H), 3.51-3.99 (m, 4 H), 4.15-4.33 (m, 1 H), 5.16-5.29 (m, 4 H), 6.54 (s, 1 H), 7.28-7.37 (m, 10 H). 13C NMR (75 MHz, CDCl3): d = -5.1, -4.3, 17.7, 21.1, 25.6, 59.1, 59.6, 66.3, 67.0, 67.4, 68.1, 68.3, 68.5, 127.5, 127.7, 128.0, 128.1, 128.3, 128.4, 128.5, 135.0, 135.4, 135.6, 156.0, 157.0, 158.2, 158.9. MS (ESI): m/z = 525.4 [M + Na+]. IR: 3409, 3272, 2955, 2856, 1722, 1268, 1097, 833, 777, 696 cm-1. Anal. Calcd for C26H38N2O6Si: C, 62.12; H, 7.62; N, 5.57. Found: C, 62.06; H, 7.55; N, 5.48.[a]D 25 -25 (c = 1, CH2Cl2) for (S,R)-2; [a]D 25 +24 (c = 1, CH2Cl2) for (R,S)-2. Compound 3: 1H NMR (300 MHz, CDCl3): d = (-0.01)-0.05 (m, 6 H), 0.81-0.82 (m, 9 H), 1.08-1.18 (m, 3 H), 3.48-4.04 (m, 4 H), 4.20-4.38 (m, 1 H), 5.14-5.30 (m, 4 H), 6.69-6.74 (m, 1 H), 7.32-7.37 (m, 10 H). 13C NMR (75 MHz, CDCl3): d = -5.3, -5.2, -4.3, -4.2, 17.6, 21.2, 21.3, 25.5, 25.6, 59.7, 59.8, 64.1, 65.8, 68.1, 68.2, 68.5, 68.7, 127.6, 128.0, 128.1, 128.2, 128.4, 128.5, 135.2, 135.5, 135.8, 156.3, 156.9, 157.6, 158.2. MS (ESI): m/z = 525.4 [M + Na+]. IR: 3401, 3270, 2953, 2855, 1721, 1256, 1072, 836, 776, 696 cm-1. Anal. Calcd for C26H38N2O6Si: C, 62.12; H, 7.62; N, 5.57. Found: C, 62.02; H, 7.35; N, 5.55. [a]D 25 -3 (c = 1, CH2Cl2) for (R,R)-3; [a]D 25 +3 (c = 1, CH2Cl2) for (S,S)-3.