메뉴 건너뛰기




Volumn 125, Issue 31, 2003, Pages 9308-9309

3-Boronoacrolein as an exceptional heterodiene in the highly enantio- and diastereoselective Cr(III)-catalyzed three-component [4+2]/allylboration

Author keywords

[No Author keywords available]

Indexed keywords

3 BORONOACROLEIN; 3 BORONOACROLEIN PINACOLATE; 6 ACETOXY 5 HEXADECANOLIDE; ACROLEIN DERIVATIVE; ALDEHYDE; ALKADIENE; BORON; CHROMIUM; PHEROMONE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0042709554     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036368o     Document Type: Article
Times cited : (121)

References (16)
  • 2
    • 0033019939 scopus 로고    scopus 로고
    • For recent reviews on multicomponent reactions, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366-374. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329.
    • (1999) Synlett , pp. 366-374
    • Weber, L.1    Illgen, K.2    Almstetter, M.3
  • 3
    • 0034665244 scopus 로고    scopus 로고
    • For recent reviews on multicomponent reactions, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366-374. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329.
    • (2000) Chem.-Eur. J. , vol.6 , pp. 3321-3329
    • Bienaymé, H.1    Hulme, C.2    Oddon, G.3    Schmitt, P.4
  • 12
    • 0042496947 scopus 로고    scopus 로고
    • note
    • Further reduction of catalyst loading slowed the cycloaddition and allowed competitive formation of a significant amount of side product from the allylboration between 4 and 3.
  • 13
    • 33751553194 scopus 로고
    • This observation, however, is consistent with a limited study with allylboronic acid 1,3-propanediol ester and benzaldehyde, which showed that polar weakly coordinating solvents gave the fastest reaction rate (THF < toluene < dichloromethane < ethyl ether): Brown, H. C.; Racherla, U. S.; Pellechia, P. J. J. Org. Chem. 1990, 55, 1868-1874.
    • (1990) J. Org. Chem. , vol.55 , pp. 1868-1874
    • Brown, H.C.1    Racherla, U.S.2    Pellechia, P.J.3
  • 14
    • 0042496946 scopus 로고    scopus 로고
    • note
    • Control experiments showed that there is no retardation nor any metal-promoted acceleration of the allylboration step with catalyst 1.
  • 15
    • 0037139565 scopus 로고    scopus 로고
    • For another recent enantioselective synthesis of 2, see: Trost, B. M.; Rhee, Y. H. J. Am. Chem Soc. 2002, 124, 2528-2533.
    • (2002) J. Am. Chem Soc. , vol.124 , pp. 2528-2533
    • Trost, B.M.1    Rhee, Y.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.