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Volumn 12, Issue 20, 2010, Pages 4474-4477

Bis-exo-2-norbornylboron triflate for stereospecific enolization of 3,3,3-trifluoropropionates

Author keywords

[No Author keywords available]

Indexed keywords

2 NORBORNENE; 2-NORBORNENE; FLUORINE DERIVATIVE; METHYLDOPA; NORBORNANE DERIVATIVE; PROPIONIC ACID DERIVATIVE;

EID: 77957825063     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1016178     Document Type: Article
Times cited : (31)

References (35)
  • 20
    • 77957852555 scopus 로고    scopus 로고
    • 3-dictyostatin
    • 3-dictyostatin
  • 22
    • 77957827594 scopus 로고    scopus 로고
    • For the aldolization of 3,3,3-trifluoropropanamides via silyl enolates, see
    • For the aldolization of 3,3,3-trifluoropropanamides via silyl enolates, see
  • 24
    • 77957857254 scopus 로고    scopus 로고
    • For the aldolization of 3,3,3-trifluoropropanamides via titanium enolates, see
    • For the aldolization of 3,3,3-trifluoropropanamides via titanium enolates, see
  • 27
    • 77957834878 scopus 로고    scopus 로고
    • The reagent - amine combination was selected on the basis of Abiko's study; see ref 8a.
    • The reagent - amine combination was selected on the basis of Abiko's study; see ref 8a.
  • 28
    • 77957850496 scopus 로고    scopus 로고
    • 19F NMR spectroscopy.
    • 19F NMR spectroscopy.
  • 29
    • 77957834717 scopus 로고    scopus 로고
    • For the assignment of the syn and anti configuration, see
    • For the assignment of the syn and anti configuration, see
  • 31
    • 77957841767 scopus 로고    scopus 로고
    • Note that the E -enolate for the esters is similar to the Z -enolate for ketones.
    • Note that the E -enolate for the esters is similar to the Z -enolate for ketones.
  • 32
    • 77957836439 scopus 로고    scopus 로고
    • 4-catalyzed aldol reaction of silicon enolates (ref 12) and TMEDA-assisted aldol reaction of titanium enolates (ref 13) of trifluoropropanamides provide syn -products selectively.
    • 4-catalyzed aldol reaction of silicon enolates (ref 12) and TMEDA-assisted aldol reaction of titanium enolates (ref 13) of trifluoropropanamides provide syn -products selectively.
  • 33
    • 77957840202 scopus 로고    scopus 로고
    • Brown and co-workers have shown that decreased bulk on boron favors syn -aldol and increased bulk favors anti -aldols for ketone enolization - aldolization.
    • Brown and co-workers have shown that decreased bulk on boron favors syn -aldol and increased bulk favors anti -aldols for ketone enolization - aldolization.
  • 35
    • 77957832773 scopus 로고    scopus 로고
    • note
    • 4), filtered, concentrated, and purified by silica gel chromatography to obtain the pure syn -aldol product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.