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Volumn 55, Issue 3, 1999, Pages 649-664

Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; SELENIDE; SULFIDE;

EID: 0033556294     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01065-5     Document Type: Article
Times cited : (66)

References (41)
  • 2
    • 0000535071 scopus 로고
    • The wittig rearrangement
    • Trost, B. M. Eds.; Pergamon Press, Oxford
    • b) Marshall, J. A. The wittig rearrangement. In Comprehensive Organic Synthesis Volume 3; Trost, B. M. Eds.; Pergamon Press, Oxford 1991; pp 975-1014.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 975-1014
    • Marshall, J.A.1
  • 3
    • 0000080952 scopus 로고
    • [2,3]-Sigmatropic rearrangement
    • Trost, B. M. Eds.; Pergamon Press, Oxford
    • c) Brückner, R. [2,3]-Sigmatropic rearrangement. In Comprehensive Organic Synthesis Volume 6; Trost, B. M. Eds.; Pergamon Press, Oxford 1991; pp 873-908.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 873-908
    • Brückner, R.1
  • 4
    • 0000639923 scopus 로고
    • Chirality transfer via sigmatropic rearrangements
    • Morrison, J. D. Eds.; Academic Press Inc., Orlando
    • d) Hill, R. K. Chirality transfer via sigmatropic rearrangements. In Asymmetric Synthesis Volume 3; Morrison, J. D. Eds.; Academic Press Inc., Orlando 1984; pp 503-572.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 503-572
    • Hill, R.K.1
  • 6
  • 26
    • 85038194402 scopus 로고    scopus 로고
    • note
    • Isolated Co(III)-salen complex 8-Br (see Experimental Section) was used for the study of solvent effect.
  • 27
    • 85038199802 scopus 로고    scopus 로고
    • note
    • It has been reported that the [2,3]Wittig rearrangement of both (E)- and (Z)-(2-alkenyloxy)acetic acid esters showed syn-selectivity (ref. 1a).
  • 28
    • 85038198952 scopus 로고    scopus 로고
    • note
    • To consider more about double diastereodifferentiation, we synthesized complex i and examined the reaction of 14 and (-)-menthyl α-diazoacetate using the complex as a catalyst. However, the reaction was sluggish, suggesting that the presence of the phenyl groups on the ethylenediamine moiety accelerated the desired reaction. The mechanism of this ligand acceleration is unclear at present. (equation presented)
  • 29
    • 85038198832 scopus 로고    scopus 로고
    • note
    • Configuration of the major diastereomer was tentatively assigned to be anti by the mechanical analogy with [2,3]sigmatropic rearrangement of the S-ylide derived from cinnamyl phenyl sulfide.
  • 35
    • 85038198796 scopus 로고    scopus 로고
    • note
    • These transition structures were searched and optimized by MOPAC Ver. 6.O. Each transition structure has only one imaginary frequency.
  • 36
    • 33751553846 scopus 로고
    • Transition structures of the sigmatropic rearrangement based on ab initia calculation were discussed: a) Wu, Y.-D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421-1423.
    • (1990) J. Org. Chem. , vol.55 , pp. 1421-1423
    • Wu, Y.-D.1    Houk, K.N.2    Marshall, J.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.