메뉴 건너뛰기




Volumn 120, Issue 33, 1998, Pages 8328-8339

Catalytic asymmetric epoxidation of aldehydes. Optimization, mechanism, and discovery of stereoelectronic control involving a combination of anomeric and cieplak effects in sulfur ylide epoxidations with chiral 1,3-oxathianes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; OXATHIIN DERIVATIVE;

EID: 0032569215     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9812150     Document Type: Article
Times cited : (118)

References (52)
  • 8
    • 84941217488 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, pp 193-246.
    • (1985) Asymmetric Synthesis , vol.5 , pp. 193-246
    • Rossiter, B.E.1
  • 21
    • 0000134379 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford
    • Doyle, M. P. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 12, pp 421-468.
    • (1995) Comprehensive Organometallic Chemistry , vol.12 , pp. 421-468
    • Doyle, M.P.1
  • 33
    • 0038816459 scopus 로고
    • 2 was prepared by adding saturated sodium carbonate to a solution of copper oxide and acetylacetone. See: Bryant, B. E.; Fernelius, W. C. Inorg. Synth. 1957, 5, 115.
    • (1957) Inorg. Synth. , vol.5 , pp. 115
    • Bryant, B.E.1    Fernelius, W.C.2
  • 34
    • 17344362302 scopus 로고    scopus 로고
    • Commercial copper acetylacetonate that had been purified by sublimation was equally effective
    • Commercial copper acetylacetonate that had been purified by sublimation was equally effective.
  • 35
    • 17344362224 scopus 로고    scopus 로고
    • It was not possible to isolate a pure sample of 7 to categorically prove its structure. The data are consistent with this product though
    • It was not possible to isolate a pure sample of 7 to categorically prove its structure. The data are consistent with this product though.
  • 41
    • 17344367647 scopus 로고    scopus 로고
    • note
    • Attempts to carry out ionic reduction of 15 failed due to competing rearrangements of the camphor skeleton. Hydrogenation using diimide and hydroboration of 15 were also unsuccessful.
  • 43
    • 17344366558 scopus 로고    scopus 로고
    • note
    • The low yield obtained with 13 is typical of 1,3-dithianes. 1,3-Dithiane itself gave 30% yield of stilbene oxide in the catalytic cycle. Also, ylide formation is quite sensitive to the steric hindrance of the sulfide, and only the more accessible sulfur should react.
  • 46
    • 17344372566 scopus 로고    scopus 로고
    • note
    • This aldehyde was chosen as it gave a slightly lower enantioselectivity compared to other aldehydes, thereby allowing us to monitor changes more easily.
  • 47
    • 17344370144 scopus 로고    scopus 로고
    • 2 was unsuccessful. No epoxides, only stilbenes, were formed
    • 2 was unsuccessful. No epoxides, only stilbenes, were formed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.