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Volumn 16, Issue 32, 2010, Pages 9835-9845

N-sulfinyl amines as a nitrogen source in the asymmetric intramolecular aza-michael reaction: Total synthesis of (-)-pinidinol

Author keywords

Aza Michael reaction; Cross metathesis; Piperidines; Pyrrolidines; Sulfinylamines

Indexed keywords

AZA-MICHAEL REACTION; CROSS METATHESIS; PIPERIDINES; PYRROLIDINES; SULFINYLAMINES;

EID: 77955869137     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000615     Document Type: Article
Times cited : (78)

References (58)
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    • For some representative examples, see: a) F. A. Davis, J. Deng, Org. Lett. 2007, 9, 1707;
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    • To the best of our knowledge, only one example of a CM reaction involving sulfinyl amines was reported in the literature: J. C. González- Gómez, F. Foubelo, M. Yus, Synlett 2008, 2702.
    • (2008) Synlett , pp. 2702
    • González-Gómez, J.C.1    Foubelo, F.2    Yus, M.3
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    • 2, gave the CM product 4b in only 21% yield
    • 2, gave the CM product 4b in only 21% yield.
  • 40
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    • A recent study of the intramolecular aza-Michael reaction under basic conditions showed a similar influence of the base in the selectivity: C. Enkisch, C. Schneider, Eur. J. Org. Chem. 2009, 5549.
    • (2009) Eur. J. Org. Chem. , pp. 5549
    • Enkisch, C.1    Schneider, C.2
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    • An analogue π-stacking interaction was previously invoked to explain the selectivity found in the intermolecular aza-Michael reaction of amines to 8-phenylmenthol-derived enoates: F. Dumas, B. Mezrhab, J. d'Angelo, J. Org. Chem. 1996, 61, 2293.
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    • Dumas, F.1    Mezrhab, B.2    D'Angelo, J.3
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    • Although under basic conditions the formation of piperidine derivatives were more favorable with p-tolyl sulfinyl amines, the corresponding CM reaction to obtain the Michael acceptor took place in only 5% yield, and we decided to use the tert-butyl sulfinyl amine in the process
    • Although under basic conditions the formation of piperidine derivatives were more favorable with p-tolyl sulfinyl amines, the corresponding CM reaction to obtain the Michael acceptor took place in only 5% yield, and we decided to use the tert-butyl sulfinyl amine in the process.
  • 43
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    • We have previously described in a preliminary communication the synergistic effect of second-generation Hoveyda-Grubbs catalyst with boron trifluoride in an analogous tandem process with carbamates as the source of the nucleophilic nitrogen
    • We have previously described in a preliminary communication the synergistic effect of second-generation Hoveyda-Grubbs catalyst with boron trifluoride in an analogous tandem process with carbamates as the source of the nucleophilic nitrogen: S. Fustero, D. Jimémnez, M. Sánchez- Roselló, C. del Pozo, J. Am. Chem. Soc. 2007, 129, 6700.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 6700
    • Fustero, S.1    Jimémnez, D.2    Sánchez-Roselló, M.3    Del Pozo, C.4
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    • 2 at -78°C furnished the desired diastereoisomer although in a modest 30% yield
    • 2 at -78°C furnished the desired diastereoisomer although in a modest 30% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.