메뉴 건너뛰기




Volumn 8, Issue 3, 2006, Pages 519-522

Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: High syn-selectivity through the effect of tri-2-furylphosphine

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; PHOSPHINE DERIVATIVE; RHODIUM; TRI 2 FURYLPHOSPHINE; TRI-2-FURYLPHOSPHINE; VINYL DERIVATIVE;

EID: 32644453569     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052859x     Document Type: Article
Times cited : (62)

References (52)
  • 1
    • 32644443321 scopus 로고
    • Though largely attributed to Würtz, the aldol reaction was reported first by Borodin: (a) von Richter, V. Ber. Deut. Chem. Ges. 1869, 2, 552 (Borodin's earliest results are cited in this article).
    • (1869) Ber. Deut. Chem. Ges. , vol.2 , pp. 552
    • Von Richter, V.1
  • 6
    • 0000244085 scopus 로고
    • For selected reviews on stereoselective aldol additions, see: (a) Heathcock, C. H. Science 1981, 214, 395.
    • (1981) Science , vol.214 , pp. 395
    • Heathcock, C.H.1
  • 11
    • 32644441427 scopus 로고    scopus 로고
    • note
    • 3- enolate.
  • 18
    • 0036291572 scopus 로고    scopus 로고
    • For reviews encompassing catalytic reductive aldol coupling, see: (a) Motherwell, W. B. Pure Appl. Chem. 2002, 74, 135.
    • (2002) Pure Appl. Chem. , vol.74 , pp. 135
    • Motherwell, W.B.1
  • 27
    • 0000191874 scopus 로고
    • For rhodium catalyzed reductive aldol couplings mediated by silane, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4809
    • Revis, A.1    Hilty, T.K.2
  • 47
    • 32644448063 scopus 로고    scopus 로고
    • note
    • As a point of reference, the lithium Z(O)-enolate of 3-pentanone aldolizes with benzaldehyde under kinetically controlled conditions to provide a 9:1 syn/anti-ratio. Upon equilibration, a 44:56 syn/anti ratio results. For further examples, see ref 3a-c.
  • 50
    • 32644445896 scopus 로고    scopus 로고
    • note
    • The stereochemical assignment of 10a is based upon single crystal X-ray diffraction analysis of the corresponding 3,5-dinitrobenzoate. The 8:1 diastereomeric ratio refers to the major isomer versus all other isomers combined.
  • 51
    • 32644437559 scopus 로고    scopus 로고
    • note
    • Enones constrained in the s-trans configuration, such as cyclohexenone, do not participate in reductive coupling.
  • 52
    • 32644446608 scopus 로고    scopus 로고
    • note
    • High levels of diastereoselectivity do not preclude reversible aldolization, provided aldolization proceeds with sufficiently high levels of kinetic stereoselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.