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Volumn 48, Issue 20, 2007, Pages 3617-3620

Phosphine triggered [3+2] allenoate-acrylate annulation: a mechanistic enlightenment

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALLENE DERIVATIVE; PHOSPHINE DERIVATIVE;

EID: 34247255386     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.030     Document Type: Article
Times cited : (174)

References (42)
  • 2
    • 29244447356 scopus 로고    scopus 로고
    • For reviews on phospine-catalyzed reactions of allenoates see:
    • For reviews on phospine-catalyzed reactions of allenoates see:. Lu X., Du Y., and Lu C. Pure Appl. Chem. 77 (2005) 1985-1990
    • (2005) Pure Appl. Chem. , vol.77 , pp. 1985-1990
    • Lu, X.1    Du, Y.2    Lu, C.3
  • 5
    • 0043076391 scopus 로고    scopus 로고
    • For highlighted explains of [3+2] phosphine-mediated allenoate-acrylate annulations in natural product synthesis, see:
    • For highlighted explains of [3+2] phosphine-mediated allenoate-acrylate annulations in natural product synthesis, see:. Du Y., and Lu X. J. Org. Chem. 68 (2003) 6463-6465
    • (2003) J. Org. Chem. , vol.68 , pp. 6463-6465
    • Du, Y.1    Lu, X.2
  • 21
    • 34247189212 scopus 로고    scopus 로고
    • note
    • Calculations were performed using the gaussian 03 suite of programs. See Supplementary data for a complete list of authors of these programs.
  • 26
    • 34247281640 scopus 로고    scopus 로고
    • note
    • b back to starting reagents requires only 13.1 kcal/mol.
  • 28
    • 34247214039 scopus 로고    scopus 로고
    • b benefits from a mere 1.1 kcal/mol of stability. (NBO Version 3.1, Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.).
  • 29
    • 34247224961 scopus 로고    scopus 로고
    • note
    • In a previous Letter addressing regioselection in phosphine catalyzed allenoate additions we have reported that α-TS1 is 1.7 kcal/mol more stable then γ-TS1 in benzene (ε = 2.27). As it is of direct relevance the calculated 1.7 kcal/mol preference for α- versus γ-addition equates to a predicted product ratio of 95:5, which is a figure consistent with experiment (α- versus γ-addition 85:15), see Ref. 6a.
  • 34
    • 34247238904 scopus 로고    scopus 로고
    • note
    • See Supplementary data for computed structure and thermochemical data.
  • 35
    • 34247207195 scopus 로고    scopus 로고
    • note
    • Interestingly, an electrostatic potential map of intermediate 7, reveals that the surface charges are well positioned to interact with a hydrogen bond donor/acceptor regions of a water molecule: see Supplementary data.
  • 36
    • 34247260054 scopus 로고    scopus 로고
    • NBO Version 3.1, Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.
  • 38
    • 34247239432 scopus 로고    scopus 로고
    • Refs. 2c and 6c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.