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Volumn 47, Issue 1, 2006, Pages 99-103

Direct organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes

Author keywords

, Unsaturated aldehydes; Asymmetric catalysis; Epoxides; Proline derivatives

Indexed keywords

ALDEHYDE; ALPHA,ALPHA DIPHENYL 2 PROLINOL; AMINO ACID DERIVATIVE; HYDROGEN PEROXIDE; IMIDAZOLE DERIVATIVE; OXYGEN; PEROXIDE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SODIUM DERIVATIVE; SODIUM PERCABONATE; SOLVENT; UNCLASSIFIED DRUG;

EID: 28544436605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.128     Document Type: Article
Times cited : (143)

References (57)
  • 16
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    • Y. Shi Acc. Chem. Res. 37 2004 488 and references cited therein
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  • 19
    • 28544451072 scopus 로고    scopus 로고
    • For a very recent chiral pyrrolidine-catalyzed epoxidation of α,β-enones see: A. Lattanzi Org. Lett. 7 2005 2579
    • (2005) Org. Lett. , vol.7 , pp. 2579
    • Lattanzi, A.1
  • 46
    • 0029018465 scopus 로고
    • Sodium percarbonate (SPC) represents one of the most powerful oxidants available. It is particularly advantageous owing to its ease of handling and storage. See: A. McKillop, and W.R. Sanderson Tetrahedron 51 1995 6145
    • (1995) Tetrahedron , vol.51 , pp. 6145
    • McKillop, A.1    Sanderson, W.R.2
  • 48
    • 28544435316 scopus 로고    scopus 로고
    • note
    • R (min) = major enantiomer 8.04 min, minor enantiomer 8.12 min.
  • 49
    • 28544441254 scopus 로고    scopus 로고
    • note
    • 9).
  • 52
    • 13444267885 scopus 로고    scopus 로고
    • 4 and concentrated in vacuo after filtration. Purification with silica gel column chromatography (EtOAc/pentane 1.7 → 1.3) furnished 10 as a thick oil (99%, 1.3 g). Jørgensen and co-workers have shown that TMS protection of diarylprolinols is an excellent strategy to achieve high stereoselectivity in organocatalytic α-fluorinations and α-sulfenylation of aldehydes see: M. Marigo, T.C. Wabnitz, D. Fielenbach, and K.A. Jørgensen Angew. Chem., Int. Ed. 44 2005 794
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 794
    • Marigo, M.1    Wabnitz, T.C.2    Fielenbach, D.3    Jørgensen, K.A.4
  • 55
    • 28544447108 scopus 로고    scopus 로고
    • note
    • 2 (0.3 mmol, 50% aqueous solution). The reaction was vigorously stirred at room temperature and monitored by chiral-phase GC analyses. The formation and enantiomeric excess of 2a was determined on a Chromasil CP-Chirasil-Dex CB-column.
  • 56
    • 28544434653 scopus 로고    scopus 로고
    • note
    • 2O). The reaction was vigorously stirred at room temperature and monitored by chiral-phase GC analyses. The formation and enantiomeric excess of the desired epoxides 2 were determined on a Chromasil CP-Chirasil-Dex CB-column.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.