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Volumn 4, Issue 7, 2002, Pages 1227-1229

Highly Diastereoselective Nitrone Cycloaddition onto a Chiral Ketene Equivalent: Asymmetric Synthesis of Cispentacin

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID; ANTIFUNGAL AGENT; BRIDGED COMPOUND; CYCLOLEUCINE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; SPIRO COMPOUND;

EID: 0037018451     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025665f     Document Type: Article
Times cited : (66)

References (45)
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    • Enantioselective cycloaddition reactions of activated nitrones onto ketene acetals have been carried out: (a) Seerden, J. P. G.; Boeren, M. M. M.; Scheeren, H. W. Tetrahedron 1997, 53, 11843.
    • (1997) Tetrahedron , vol.53 , pp. 11843
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    • 0000137347 scopus 로고    scopus 로고
    • Although dithiolane 1 had been employed in intermolecular nitrone cycloadditions, we chose to work on the dithiane derivative 3 as the synthesis of such substituted alkenes had already been successfully achieved and employed in epoxidation: (a) Aggarwal, V. K.; Barrell, J. K.; Worrall, J. M.; Alexander, R. J. Org. Chem. 1998, 63, 7128. In related Diels-Alder cycloadditions, dithiolane 1 was found to be more reactive and more selective than the dithiane analogue of 1:
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    • Oxidation of 2-carboethoxy-1,3-dithiane and other 2-substituted 1,3-dithianes with (+)-DET gave the (R)-sulfoxide as noted in: (a) Aggarwal, V. K.; Evans, G. R.; Moya, E.; Dowden, J. J. Org. Chem. 1992, 57, 6390.
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  • 33
    • 0042904009 scopus 로고    scopus 로고
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    • Collect. , vol.7 , pp. 168-171
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    • 0342894708 scopus 로고    scopus 로고
    • For another example of the acceleration of a palladium-catalysed hydrogenolysis using triethylamine as an additive, see: Effenberger, F.; Jager, J. Chem. Eur. J. 1997, 3, 1370.
    • (1997) Chem. Eur. J. , vol.3 , pp. 1370
    • Effenberger, F.1    Jager, J.2
  • 37
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    • For a review on the use of the sulfinyl group in asymmetric synthesis, see: (a) Carreno, M. Chem. Rev. 1995, 95, 1717-1760.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.