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Tetrahedron Letters
Volumn 27, Issue 37, 1986, Pages 4507-4510
Asymmetric diels-alder reaction. Cooperative blocking effect in organic synthesis
Author keywords

[No Author keywords available]
Indexed keywords

EID: 0001013175     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)84991-6     Document Type: Article
Times cited : (114)
References (14)
  • 3
    • 84918474539 scopus 로고    scopus 로고
    • Recent review: L. A. Paquette, in “Asymmetric Synthesis, Vol. 3,” ed by Morrison, J. D., Academic Press, Inc., Orlando, Florida.
  • 6
    • 84918474538 scopus 로고    scopus 로고
    • The Lewis acid coordinated fumarate is considered to exist in the s-trans form predominantly. Thus, the two (-)-menthyl groups should cooperatively cover the re face of the molecule. In the thermal reaction, on the other hand, the free fumarate is regarded to exist as an equilibrium mixture of s-trans and s-cis conformations.
  • 7
    • 84918474537 scopus 로고    scopus 로고
    • 7 the reaction with anthracene revealed a complete diastereoselection even by aluminum chloride catalysis at ambient temperature.
  • 8
    • 0001467612 scopus 로고
    • Tolbert and Ali had proposed a concept of cooperativity in connection with the synchronisity of the concerted reactions.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2104
    • Tolbert1    Ali2
  • 11
    • 0006297837 scopus 로고
    • Recently, Masamune et al. described the usefulness of the concept of double asymmetric induction in organic synthesis.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4589
    • Tolbert1    Ali2
  • 13
    • 84918474536 scopus 로고    scopus 로고
    • The following procedure illustrates the method: A solution of (-)dimenthyl fumarate (9.42 g, 24 mmol) in toluene (144 ml) was treated with diethylaluminum chloride (24 ml of a 1 M hexane solution) at −78°C under nitrogen. The mixture was stirred for 15 min and to the resulting orange solution was added cyclopentadiene (5.85 ml, 72 mmol) dropwise at the same temperature. Acidic workup was conducted and the product was isolated by column chromatography on silica gel (11.0 g).
  • 14
    • 84918474535 scopus 로고    scopus 로고
    • The MTPA esters of diols derived from the Diels-Alder adducts of dimethyl fumarate (both thermal and aluminum chloride catalyzed reactions) showed two peaks (1:1) on HPLC analysis.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.