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Volumn 18, Issue 9, 2007, Pages 1115-1123

Synthesis of oxazolidines using DMSO/P4O10 as a formaldehyde equivalent

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; ETHYL 3 (METHOXYPHENYL) 4 PHENYL OXAZOLIDINE 5 CARBOXYLATE; FORMALDEHYDE; OXAZOLIDINE DERIVATIVE; OXIDE; TETRAPHOSPHORUS DECAOXIDE; UNCLASSIFIED DRUG;

EID: 34249872184     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.04.017     Document Type: Article
Times cited : (27)

References (53)
  • 4
    • 34249887562 scopus 로고    scopus 로고
    • Wuts, P. G. M.; Kelly, R. C. PCT Int. Appl., 1997, 67.
  • 25
    • 34249885237 scopus 로고    scopus 로고
    • note
    • Commercially available starting material (ethyl 3-phenylglycidate) is a mixture of 14% cis, 85% trans, and an unidentified impurity (1%) as established by GC-MS, SPB-5 column. The mixture can be separated by chromatography, with the cis isomer eluting first. The ring opening and the following oxidation reactions can also be carried with the commercial mixture of the cis and trans ethyl-3-phenylglycidate since the trans and cis oxazolidines are also easily separated by chromatography.
  • 38
    • 34249896075 scopus 로고    scopus 로고
    • note
    • The oxazolidine ring has an envelope conformation with the O atom out of the plane formed by the four other atoms. The torsion angles inside the five-membered ring are N3-C4-C5-O1 = -26.4(4)°, C4-C5-O1-C2 = 43.5(4)°, C5-O1-C2-N3 = -42.7(4)°, O1-C2-N3-C4 = 25.5(4)°, and C2-N3-C4-C5 = 0.9(4)°. The N-C bond distances inside the ring are 1.456(6) and 1.463(6) Å, while the N-C11 is shorter (1.395(6) Å). In the oxazolidine ring, the C-O bonds are 1.400(6) and 1.434(5) Å, while the C-C bond is 1.553(6) Å. For the ester group, the C{double bond, long}O bond (ave. 1.201(5) Å) is shorter than the C-O bond (ave. 1.340(5) Å) as expected. The H atoms on C4 and C5 are cis to each other. The molecules are stabilized in the crystal only by van der Waals interactions. The CIF tables of the crystal 4b have been deposited in the Cambridge Data File Centre. The deposit number is CCDC 619250. This material is available free of charge via the Internet at http://pubs.acs.org.
  • 39
    • 34249886205 scopus 로고
    • Academic Press, London
    • Haines A.H. Methods for the Oxidation of Organic Compounds. Best Synthetic Methods Series (1988), Academic Press, London 91-127
    • (1988) Best Synthetic Methods Series , pp. 91-127
    • Haines, A.H.1
  • 48
    • 34249900101 scopus 로고    scopus 로고
    • Wang, J. Chemoenzymatic Synthesis of Enantiopure Oxazolidines and β-Lactams. M.Sc. Thesis, March 2007.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.