Enantioselective protonation of amide enolates derived from piperidine-2-carboxylic acid

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7181-7182

  Martin, Juliette ^a   Lasne, Marie Claire ^a   Plaquevent, Jean Christophe ^b   Duhamel, Lucette ^b  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MUSCARINIC RECEPTOR BLOCKING AGENT; PIPERIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030679752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01705-X     Document Type: Article

References (18)

1. a) Duhamel, L. C. R. Acad. Sciences 1976, 282C, 125-127;
2. b) Matsushita, H.; Tsujino, Y.; Noguchi, M.; Saburi, M.; Yoshikawa, S. Bull. Soc. Chim. Jpn. 1978, 51, 862-865 and references cited therein.
3. Duhamel, L.; Plaquevent, J.-C. J. Am. Chem. Soc., 1978, 100, 7415-7416.
4. a) Duhamel, L.; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr., 1984, II, 421-430.
5. b) Fehr, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2567-2587 and references cited therein.
6. a) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1991, 113, 5483-5485;
7. b) Vedejs, E.; Lee, N.; Sakata, S.T. J. Am. Chem. Soc. 1994, 116, 2175-2176;
8. c) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891-900.
9. Enantioselective protonation under the influence of a chiral amine (or its salt): a) Duhamel, L.; Plaquevent, J.-C. Tetrahedron Lett. 1980, 21, 2521-2524.
10. b) Hogeveen, H.; Zwart, L. Tetrahedron Lett. 1982, 23, 105-108;
11. c) Yasukata, T.; Koga, K., Tetrahedron: Asymmetry 1993, 4, 35-38;
12. d) Fuji, K.; Tanaka, K.; Miyamoto, H. Tetrahedron: Asymmetry 1993, 4, 247-249.
13. 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidine-1-yl] ethylamino]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one.
14. Perrio-Huard, C.; Ducandas, C.; Lasne, M.-C.; Moreau B. J. Chem. Soc. Perkin I 1996, 2925-2931.
15. Diamine (+)-3 was obtained from recrystallized 1-[5-chloro-2-(methylamino)-phenyl]-1,2,3,4-tetrahydroisoquinoline tartrate (Aldrich).
16. The enantiomeric excess was determined by HPLC on chiral OD-type or Chirose-Bond stationary phase, 1 x d: 250 x 4.6 mm; eluents : n-heptane/ iPrOH (v: v 95:5); flow : 0.6 mL.min-1;λ: 220 nm. The configurations were deduced from independent syntheses of both enantiomers using commercially available (R)-or (S)-piperidine-2-carboxylic acid.
17. 3) (S)-1: -24.6; (S)-2: -40.
18. Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Scwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure & Appl. Chem. 1994, 66, 1479.