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Volumn 4, Issue 4, 2007, Pages 228-231

Asymmetric induction in Darzens condensation by means of (R)-5,5-dimethyl-4-phenyloxazolidin-2-One as an effective chiral auxiliary

Author keywords

Asymmetric induction; Chiral auxiliary; Darzens reaction; diastereo selectivity; Glycidic ester; N acyl oxazolidin 2 one

Indexed keywords


EID: 35649002660     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807781024327     Document Type: Article
Times cited : (11)

References (43)
  • 4
    • 0000784042 scopus 로고
    • For a Review, see:, Trost, B. M, Fleming, I, Heathcock, C. H, Eds; Pergamon: Oxford
    • For a Review, see: Rosen, T. In "Comprehensive Organic Synthesis", Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds; Pergamon: Oxford, 1991; Vol. 2, pp. 409.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 409
    • Rosen, T.1
  • 31
    • 35648980212 scopus 로고    scopus 로고
    • 3): δ 1.05 (s, 3H), 1.67 (s, 3H), 4.21 (s, 2H), 5.30 (s, 1H), 7.10-7.30 (m, 5H).
    • 3): δ 1.05 (s, 3H), 1.67 (s, 3H), 4.21 (s, 2H), 5.30 (s, 1H), 7.10-7.30 (m, 5H).
  • 32
    • 35648940447 scopus 로고    scopus 로고
    • Typical procedure for asymmetric Darzens condensation: A solution of DBU in THF (0.76 g, 5 mmol in 10 mL THF) was added dropwise via syringe to a solution of the adduct 2 (1.56 g, 5 mmol) and benzaldehyde (0.53 g, 5 mmol) in THF (20 mL) in a 50-mL round-bottom flask, at 0 °C under an atmosphere of dry nitrogen. After the reaction was completed (5h, it was quenched with 5 mL of 25% aqueous solution of NaHCO3 and extracted with diethyl ether (3×25 mL, The combined organic layer were dried over MgSO4, and evaporated in vacuo to provide crude products which was purified by preparative TLC (n-hexane/ethyl acetate 3:1) to give 3a and 4a. Selected data for compounds 3a-g: Compound 3a: white solid, mp 151-153 °C, Found: C, 71.17; H, 5.70; N, 4.13 C20H19NO4 requires C, 71.21; H, 5.63; N, 4.15, IR film, cm-1, 3040, 1756, 1497, α]26D, 56.2
    • 4, and evaporated in vacuo to provide crude products which was purified by preparative TLC (n-hexane/ethyl acetate 3:1) to give 3a and 4a. Selected data for compounds 3a-g: Compound 3a: white solid, mp 151-153 °C,(...)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.