Rational design of novel axially chiral NADH models based on configurational control of atropisomeric lactams

Tetrahedron Letters

Volumn 42, Issue 22, 2001, Pages 3713-3716

  Vasse, Jean Luc ^a   Dupas, Georges ^a   Duflos, Jack ^a   Quéguiner, Guy ^a   Bourguignon, Jean ^a   Levacher, Vincent ^a  

^a IRCOF   (France)

Author keywords

Asymmetric reduction; Atropisomeric lactam; Conformational atropisomers; NADH

Indexed keywords

CARBON; FORMIC ACID DERIVATIVE; LACTAM DERIVATIVE; MANDELIC ACID DERIVATIVE; MANDELIC ACID METHYL ESTER; PHENYLGLYOXYLIC ACID METHYL ESTER; REAGENT; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0035962982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)00555-X     Document Type: Article

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18. 3, 200 MHz). Compound 2: δ 0.84 (3H, t, J=7.0 Hz), 1.92-2.42 (4H, m), 2.78-2.95 (2H, m), 3.03 (3H, s), 3.32 (1H, six, J=7.0 Hz), 3.58 (1H, d, J =18.0 Hz), 3.82 (1H, six, J=7.0 Hz), 3.86 (3H, s), 3.90 (3H, s), 4.35 (1H, d, J=18.0 Hz), 4.67 (1H, dd, J=7.0 Hz, J=3.8 Hz), 6.55 (1H, s), 6.68 (1H, s), 7.12-7.22 (3H, m). Compound 6: δ 1.04 (3H, t, J=7.0 Hz), 2.08 (2H, m), 2.35 (2H, m), 2.86-3.03 (2H, m), 3.57 (1H, quint, J=7.0 Hz,) 3.84 (1H, quint, J=7.0 Hz), 4.07 (3H, s), 4.21 (3H, s), 4.41 (3H, s), 4.93 (1H, m), 7.36 (1H, s), 7.37-7.44 (4H, m), 7.61 (1H, s), 9.10 (1H, s). Compound 5: δ 1.07 (3H, t, J=7.0 Hz), 1.90-2.15 (3H, m), 2.36 (1H, m), 2.70-2.82 (1H, m), 2.92-3.05 (1H, dt, J=17.0, 3.5 Hz), 3.55 (1H, six, J=7.0 Hz), 4.00 (1H, six, J=7.0 Hz), 4.02 (3H, s), 4.04 (3H, s), 4.86 (1H, m), 7.13 (1H, s), 7.20 (1H, d, J=7.5 Hz), 7.38 (1H, t, J=7.5 Hz), 7.96 (1H, d, J=7.5 Hz), 8.62 (1H, s).
19. Molecular mechanics (MM2) and MOPAC (PM3) program led to the same conformation.
20. 2O/cyclohexane:2/1). Yield: 89%. Enantiomeric excesses were determined by HPLC analysis using a Chiracel OD column (250×4.6 mm, 10 μm). Chromatographic conditions: injection: 20 μL (0.5 mg of methyl mandelate in 10 mL of hexane). Eluent: hexane/2-propanol: 90/10. Flow rate: 1 mL/min. Pressure: 300 psi. Temperature: 22°C. UV detection: λ=235 nm. Retention time: 9.2 min [(S)-enantiomer] and 14.8 min [(R)-enantiomer]. Enantiomeric excess: 92% (S).