메뉴 건너뛰기




Volumn , Issue 1, 2009, Pages 71-74

Diastereoselective synthesis of functionally diverse substituted pipecolic acids

Author keywords

Arylpiperidine; Lactam enolate alkylations; Pipecolic acid; Piperidinone; Suzuki Miyaura coupling

Indexed keywords


EID: 62349117020     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087477     Document Type: Article
Times cited : (5)

References (55)
  • 1
    • 0016724057 scopus 로고    scopus 로고
    • See, for example: (a) Rapamycin: Vézina, C.; Kudelski, A.; Sehgal, S. N. J. Antibiotics 1975, 28, 721.
    • See, for example: (a) Rapamycin: Vézina, C.; Kudelski, A.; Sehgal, S. N. J. Antibiotics 1975, 28, 721.
  • 5
    • 0032575194 scopus 로고    scopus 로고
    • Tetrazomine: Scott, J. D.; Tippie, T. N.; Williams, R. M. Tetrahedron Lett. 1998, 39, 3659.
    • (e) Tetrazomine: Scott, J. D.; Tippie, T. N.; Williams, R. M. Tetrahedron Lett. 1998, 39, 3659.
  • 7
    • 0035920626 scopus 로고    scopus 로고
    • See, for example: (a) Mersinines A and B: Kam, T.-S.; Subramaniam, G.; Lim, T.-M. Tetrahedron Lett. 2001, 42, 5977.
    • See, for example: (a) Mersinines A and B: Kam, T.-S.; Subramaniam, G.; Lim, T.-M. Tetrahedron Lett. 2001, 42, 5977.
  • 8
    • 34548640515 scopus 로고    scopus 로고
    • Sanguinones: Peters, S.; Spiteller, P. J. Nat. Prod. 2007, 70, 1274.
    • (b) Sanguinones: Peters, S.; Spiteller, P. J. Nat. Prod. 2007, 70, 1274.
  • 9
    • 62349084661 scopus 로고    scopus 로고
    • Bipleiophylline: Kam T.-S., Tan S.-J., Ng S.-W., Komiyama K.; Org. Lett.; 2008, in press
    • (c) Bipleiophylline: Kam T.-S., Tan S.-J., Ng S.-W., Komiyama K.; Org. Lett.; 2008, in press
  • 29
    • 0032969622 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Couty, F. Amino Acids 1999, 16, 297.
    • (1999) Amino Acids , vol.16 , pp. 297
    • Couty, F.1
  • 39
    • 2042507954 scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
    • (1995) Chem. Rev , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
  • 42
    • 62349084965 scopus 로고    scopus 로고
    • 4. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography (generally hexane-EtOAc, 8:2).
    • 4. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography (generally hexane-EtOAc, 8:2).
  • 43
    • 62349106966 scopus 로고    scopus 로고
    • Data for Selected Compound: (2S,4S, Di-tert-butyl 6-Oxo-4-phenylpiperidine-1,2-dicarboxylate (4a) From 3a (119 mg, 0.32 mmol) was obtained 4a as a white solid (120 mg, 100, α]D -28.6 (c 1.04, CHCl 3, mp 142.5-147.5°C. IR (KBr, 2982, 2934, 1731, 1703, 1605, 1495, 1473, 1459, 1392, 1365, 1283, 1270, 1237, 1153, 1135, 1099, 1042, 1029, 1015 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.37 (t, 2 H, J, 7.2 Hz, 7.29 (t, 1 H, J, 7.4 Hz, 7.21 (d, 2 H, J, 7.2 Hz, 4.60 (dd, 1 H, J, 10.0, 6.6 Hz, 3.17-3.08 (m, 1 H, 2.85-2.79 (m, 1 H, 2.64 (dd, 1 H, J, 16.8, 13.0 Hz, 2.59-2.52 (m, 1 H, 2.03-1.94 (m, 1 H, 1.56 (s, 9 H, 1.48 (s, 9 H) ppm. 13C NMR 100 MHz, CDCl3, δ, 170.2, 169.6, 152.1, 141.7, 128.6, 126.9, 126.1, 83.4, 81.9, 58.7, 41.5, 36.7, 33.4, 27.5 ppm. HRMS: m/z cal
    • +.
  • 51
    • 62349092091 scopus 로고    scopus 로고
    • Data for Selected Compound: (2S,4S,5R)-Di-tert-butyl 5-Allyl-6-oxo-4- phenylpiperidine-1,2-dicarboxylate (5) From 4a (1.06 g, 2.82 mmol) was obtained 5 as a white solid (904 mg, 77, α]D -133.1 (c 1.41, CHCl3, mp 115-117°C. IR (KBr, 2980, 1728, 1707, 1457, 1366, 1283, 1248, 1225, 1145, 1028 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.36-7.28 (m, 2 H, 7.28-7.20 (m, 1 H, 7.18-7.08 (m, 2 H, 5.70 (dddd, 1 H, J, 17.0, 10.1, 8.6, 5.7 Hz, 4.97 (d, 1 H, J, 10.1 Hz, 4.85 (d, 1 H, J, 17.1 Hz, 4.47 (dd, 1 H, J, 10.3, 6.2 Hz, 2.92 (dt, 1 H, J, 11.8, 11.8, 3.9 Hz, 2.73 (td, 1 H, J, 11.9, 4.5, 4.5 Hz, 2.66-2.51 (m, 1 H, 2.38 (ddd, 1 H, J, 13.7, 6.1, 4.0 Hz, 2.06-1.93 (m, 2 H, 1.51 (s, 9 H, 1.42 (s, 9 H) ppm. 13C NMR 75 MHz, CDCl3, δ, 171.8, 170
    • +.
  • 52
    • 62349094023 scopus 로고    scopus 로고
    • Data for Selected Compound: (2S,4R, Di-tert-butyl 4-Phenylpiperidine-1,2-dicarboxylate (8) From 4a (30 mg, 0.08 mmol) was obtained 8 as a colorless gum (25 mg, 93, α]D -15.6 (c 0.95, CHCl3, IR (NaCl, 2976, 1738, 1699, 1602, 1478, 1454, 1393, 1366, 1249, 1150, 1028 cm -1. 1H NMR (400 MHz, CDCl3, δ (rotamers, 7.35-7.31 (m, 2 H, 7.26-7.21 (m, 3 H, 4.25-4.21 (m, 1 H, 3.75-3.56 (m, 2 H, 2.88-2.80 (m, 1 H, 2.28-2.22 (m, 1 H, 2.14-2.02 (m, 2 H, 1.87-1.78 (m, 1 H, 1.49 (s, 9 H, 1.42 (s, 9 H, 13C 100 MHz, CDCl3, δ, 171.3, 155.4, 144.6, 128.2, 126.6, 126.0, 80.6, 79.7, 56.1, 37.1, 32.4, 29.8, 28.0, 27.6 ppm. HRMS: m/z calcd for C21H 31NO4: 361.22531; found: 362.23232 [M, H
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.