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Volumn 69, Issue 12, 2004, Pages 4013-4018

Stereoselective conjugate addition of benzyl phenylsulfonyl carbanions to enoates derived from D-mannitol

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CHEMICAL BONDS; KETONES; PHASE EQUILIBRIA; REACTION KINETICS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 2942529003     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035427d     Document Type: Article
Times cited : (6)

References (57)
  • 13
    • 0006066291 scopus 로고    scopus 로고
    • (h) Shibasaki, M. J. Am. Chem. Soc, 2000, 122, 6506. Shibasaki, M.; Sasai, H.; Arai, T Angew. Chem., Int. Ed. Engl. 1997, 36, 1237.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6506
    • Shibasaki, M.1
  • 46
    • 0001695687 scopus 로고
    • (a) Piazza, C.; Millot, N.; Knochel, P. J. Organomet. Chem. 2001, 624, 88. Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5425.
    • (1992) J. Org. Chem. , vol.57 , pp. 5425
    • Jubert, C.1    Knochel, P.2
  • 50
    • 2942527807 scopus 로고    scopus 로고
    • note
    • Phenylnitromethane was previously used by our group as synthetic equivalent of benzyl carbanions in conjugate addition to E-1a,b. However, neither the synthesis of oxygenated phenylnitromethane derivatives nor the conjugate addition of these compounds to E-1a,b led to satisfactory results.
  • 51
    • 33947303222 scopus 로고
    • Benzyl phenylsulphones were prepared as described in Meek, J. S.; Fowler, J. S. J. Org. Chem. 1968, 33, 3422.
    • (1968) J. Org. Chem. , vol.33 , pp. 3422
    • Meek, J.S.1    Fowler, J.S.2
  • 56
    • 2942617436 scopus 로고    scopus 로고
    • note
    • H3,4 are identical and they react with phenylsuphonyl carbanions with the same stereoselectivity, one can accept that the conformational equilibrium around C3-C4 bond is little affected by the nature of the ester moiety.
  • 57
    • 2942559327 scopus 로고    scopus 로고
    • note
    • 1, leading to syn adducts.5b The reasons for these different preferences are being studied in our laboratory.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.