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Volumn , Issue 14, 2007, Pages 2242-2246

An efficient synthesis of azetidine-2,3-diones from L-(+)-diethyl tartrate

Author keywords

Cycloaddition; Imines; Lactams; Spiro compounds; Stereoselective synthesis

Indexed keywords

AZETIDINE 2,3 DIONE; AZETIDINE DERIVATIVE; BETA LACTAM; TARTARIC ACID; TARTARIC ACID DIETHYL ESTER; UNCLASSIFIED DRUG;

EID: 34548836835     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985563     Document Type: Article
Times cited : (14)

References (61)
  • 2
    • 0004030277 scopus 로고
    • Morin, R. B, Gorman, M, Eds, Academic Press: New York
    • (b) Chemistry and Biology of β-Lactam Antibiotics, Vol. 1; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
    • (1982) Chemistry and Biology of β-Lactam Antibiotics , vol.1
  • 3
    • 0004030277 scopus 로고
    • Morin, R. B, Gorman, M, Eds, Academic Press: New York
    • (c) Chemistry and Biology of β-Lactam Antibiotics, Vol. 2; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
    • (1982) Chemistry and Biology of β-Lactam Antibiotics , vol.2
  • 4
    • 0004030277 scopus 로고
    • Morin, R. B, Gorman, M, Eds, Academic Press: New York
    • (d) Chemistry and Biology of β-Lactam Antibiotics, Vol. 3; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
    • (1982) Chemistry and Biology of β-Lactam Antibiotics , vol.3
  • 7
    • 34548820940 scopus 로고    scopus 로고
    • The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
    • (g) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
  • 52
    • 34548854482 scopus 로고    scopus 로고
    • Typical Procedure for Spiro-β-lactams 5a and 6a: A solution of acid chloride 3 (0.371 g, 1.84 mmol) in anhyd dichloromethane (10 mL) was added dropwise over a period of 20-30 min to a solution of imine 4a (0.296 g, 1.23 mmol) and triethyl amine (0.77 mL, 5.53 mmol) in anhyd dichloromethane (20 mL) at -40°C. After the addition was complete the solution was allowed to attain r.t. and stirred for 15 h (TLC, The reaction mixture was then diluted with dichloromethane and washed with H2O (2 × 10 mL) and sat. brine solution (10 mL, The combined organic layer was dried over anhyd Na2SO4, filtered and concentrated under reduced pressure to get the crude diastereomeric mixture of 5a and 6a (0.480 g, 70, 1H NMR of the crude product showed a 60:40 mixture of diastereomers which were separated by careful flash column chromatography [PE-EtOAc 8:2, 3S,4S,8R
    • 3): δ =...
  • 53
    • 34548860055 scopus 로고    scopus 로고
    • X-ray Data for 5a and 8b: Single crystals of the 5a and 8b were grown by slow evaporation of the solution mixture in EtOAc and PE. The X-ray data of 5a-8b were collected on a SMART APEX CCD single crystal X-ray diffractometer with omega and phi scan mode and different number of scans and exposure times for different crystals using λ(MoKα, 0.71073 Å radiation at T, 293 (2) K with oscillation/frame, 0.3°, maximum detector swing angle, 30.0°, beam center, 260.2, 252.5, in plane spot width, 1.24. All the data were corrected for Lorentzian, polarization and absorption effects using SAINT and SADABS programs. The crystal structures were solved by direct method using SHELXS-97 and the refinement was performed by full matrix least squares of F2 using SHELXL-97.33 Crystal Data for 5a C24H 27NO7, M, 441.47; crystal dimensions: 0.52 x 0.47 x 0.33 mm, multirun d
    • 2 = 0.1552. X-ray analysis revealed the stereochemistry at C(3) and C(4) positions. The end atom C(19) had positional disorder. The supplementary crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/ data_request/cif. Please quote the reference number CCDC 647624.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.