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Volumn 15, Issue 23, 2004, Pages 3775-3781

Synthesis of chiral pentacyclo-undecane macrocycles and their use in enantioselective Michael addition reactions

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROPROPANE; CHALCONE; CYCLODECANE DERIVATIVE; DECANE; MACROCYCLIC COMPOUND; METHOXIDE SODIUM; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 9644273951     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.10.015     Document Type: Article
Times cited : (21)

References (35)
  • 22
    • 9644287187 scopus 로고    scopus 로고
    • note
    • Steric hindrance is not the only factor that would influence the reaction. The acidity of 2-nitropropane is much higher than for methyl phenylacetate
  • 25
    • 9644286808 scopus 로고    scopus 로고
    • note
    • Cram and Sogah (see Ref. 10) reported 67% ee at 25°C and 99% ee at -78°C for the Michael addition reaction in Scheme 1. The PCU macrocycles gave 90-92% ee at 25°C for the Michael addition reaction in Scheme 2 and, should in analogy to Cram's result, give a higher % ee at lower temperatures
  • 26
    • 9644297062 scopus 로고    scopus 로고
    • note
    • The fact that NaOMe, in the presence of the PCU macrocycles, is unable to initiate the reaction between methyl phenylacetate 1 and methyl acrylate 2, but able to initiate the reaction between 2-nitropropane 4 and chalcone 5 is possible due to both steric and electronic factors. Phenyl acetate is sterically more hindered than 2-nitropropane. Its α-hydrogen is also less acidic than for 2-nitropropane
  • 27
    • 9644298619 scopus 로고    scopus 로고
    • note
    • In the absence of experimental details the correction for zero point energy was not incorporated. Solvent effects were also omitted in order to simplify the model
  • 35
    • 9644307782 scopus 로고    scopus 로고
    • Alchemy is a registered product of Tripos, Inc., St. Louis, MO, USA
    • Alchemy is a registered product of Tripos, Inc., St. Louis, MO, USA


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.