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Volumn 74, Issue 13, 2009, Pages 4747-4752

Diastereoselective domino reactions of chiral 2-substituted 1-(2′,2′,3′,3′-tetramethylcyclopropyl)-alkan-1-ols under Friedel-crafts conditions

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; ALKANOLS; CARBONYL ADDITION; CHEMICAL EQUATIONS; CHEMICAL YIELDS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; DOMINO REACTIONS; FRIEDEL-CRAFTS; FRIEDEL-CRAFTS ALKYLATION; FRIEDEL-CRAFTS ALKYLATION REACTION; METHYLTHIOPHENE; REACTION CONDITIONS; RING OPENING; SUBSTITUTION PRODUCTS;

EID: 67649631273     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900445c     Document Type: Article
Times cited : (15)

References (40)
  • 8
    • 67649595836 scopus 로고    scopus 로고
    • One reviewer has raised the question whether the cyclopropylcarbinyl cation and the depicted tertiary cation resulting from alcohol 1 prior to rearrangement to cation 2 are different species or just different Lewis structures representing the same cation. While we have not studied this issue more closely, we feel that the rearrangement is easier to understand in the way it is drawn in Figure 1. However, one could of course accommodate this concern by replacing the reaction arrow with a double-headed arrow (↔) representing mesomeric structures
    • One reviewer has raised the question whether the cyclopropylcarbinyl cation and the depicted tertiary cation resulting from alcohol 1 prior to rearrangement to cation 2 are different species or just different Lewis structures representing the same cation. While we have not studied this issue more closely, we feel that the rearrangement is easier to understand in the way it is drawn in Figure 1. However, one could of course accommodate this concern by replacing the reaction arrow with a double-headed arrow (↔) representing mesomeric structures.
  • 22
    • 67649625821 scopus 로고    scopus 로고
    • For previous work in this area, see
    • For previous work in this area, see: Ishikawa, T.; Aikawa, T.; Mori, Y.; Saito, S. Org. Lett. 2008, 10, 3037-3040.
    • (2008) Org. Lett. , vol.10 , pp. 3037-3040
    • Ishikawa, T.1    Aikawa, T.2    Mori, Y.3    Saito, S.4
  • 33
    • 0003942864 scopus 로고
    • John Wiley & Sons: New York, It should be noted, however, that the conformational A value provides only a rough estimate for the size of a functional group
    • Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 696-697. It should be noted, however, that the conformational A value provides only a rough estimate for the size of a functional group.
    • (1994) Stereochemistry of Organic Compounds , pp. 696-697
    • Eliel, E.L.1    Wilen, S.H.2
  • 40
    • 67649601327 scopus 로고
    • Japanese Patent 06271484 A 19940927
    • Shinzo, S. Japanese Patent 06271484 A 19940927, 1994.
    • (1994)
    • Shinzo, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.