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Volumn 70, Issue 23, 2005, Pages 9399-9406

Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBOXYLATION; NITROGEN COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 27744483875     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051495j     Document Type: Article
Times cited : (63)

References (109)
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    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10677-10678
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  • 14
    • 0038653828 scopus 로고    scopus 로고
    • Merck & Co., Inc. Whitehouse Station, NJ
    • Merck Index, 13th ed. 2001, p1560, Merck & Co., Inc. Whitehouse Station, NJ.
    • (2001) Merck Index, 13th Ed.
  • 22
    • 1542375289 scopus 로고    scopus 로고
    • For recent review on the ring-opening reaction of aziridines, see: Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 43
    • 21344485305 scopus 로고
    • Low yields in some cases may be caused by dimerization of starting aldehydes. See: Laitalainen, T.; Kuronen, P.; Hesso, A. Org. Pre. Pro. Int. 1993, 25, 597-599.
    • (1993) Org. Pre. Pro. Int. , vol.25 , pp. 597-599
  • 44
    • 0001425679 scopus 로고
    • For the basic discussion on the coupling constant, see: Foglia, T. A.; Swern, D. J. Org. Chem. 1969, 34, 1680-1684.
    • (1969) J. Org. Chem. , vol.34 , pp. 1680-1684
    • Foglia, T.A.1    Swern, D.2
  • 47
    • 27744510665 scopus 로고    scopus 로고
    • note
    • We have observed that the ring-opening reaction of 3-arylaziridine-2- carboxylates is greatly dependent upon the nature of substituent on the aryl group. These results will be reported elsewhere in the near future.
  • 48
    • 27744464769 scopus 로고    scopus 로고
    • note
    • 2CS).
  • 50
    • 0002694812 scopus 로고
    • Cevc, G., Ed.; Dekker: New York
    • For reviews of the synthesis of sphingosine, see: Byun, H.-S.; Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Dekker: New York, 1993; pp 97-140.
    • (1993) Phospholipids Handbook , pp. 97-140
    • Byun, H.-S.1    Bittman, R.2
  • 54
    • 0011447582 scopus 로고    scopus 로고
    • Gunstone, F. D., Ed.; Sheffield Academic: Schefield UK
    • Jung, K.-H.; Schmidt, R. R. In Lipid Synthesis and Manufacture; Gunstone, F. D., Ed.; Sheffield Academic: Schefield UK, 1999; pp 208-249.
    • (1999) Lipid Synthesis and Manufacture , pp. 208-249
    • Jung, K.-H.1    Schmidt, R.R.2
  • 105
    • 0033800394 scopus 로고    scopus 로고
    • Discrimination between activated and unactivated (or nonactivated) is dependent upon a substituent on the nitrogen atom of aziridine systems and the former is used in the cases of electron-attractive group such as an acyl group; see, McCoull, W.; Davis, F. A. Synthesis 2000, 1347-1365.
    • (2000) Synthesis , pp. 1347-1365
    • McCoull, W.1    Davis, F.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.