메뉴 건너뛰기




Volumn , Issue 5, 2006, Pages 761-765

A Brønsted acid and Lewis base organocatalyst for the aza-Morita-Baylis-Hillman reaction

Author keywords

Bifunctional catalyst; Br nsted acid; Enantioselective aza Morita Baylis Hillman reaction; Lewis base; Organocatalysis

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; 3 (3 DIPHENYLPHOSPHINOPHENYL) 2,2' DIHYDROXY 1,1' BINAPHTHYL; IMINE; KETONE; LEWIS BASE; N TOSYLIMINE; UNCLASSIFIED DRUG;

EID: 33645395732     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-933112     Document Type: Article
Times cited : (134)

References (39)
  • 21
    • 15744396095 scopus 로고    scopus 로고
    • Aza-MBH reactions are accelerated in the presence of acidic and basic catalysts. See: (a) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3680
    • Matsui, K.1    Takizawa, S.2    Sasai, H.3
  • 30
    • 0344874579 scopus 로고    scopus 로고
    • Asymmetric catalysts bearing metal coordination units on the axial linkage have been reported. See: (a) Aikawa, K.; Mikami, K. Angew. Chem. Int. Ed. 2003, 42, 5458.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5458
    • Aikawa, K.1    Mikami, K.2
  • 33
    • 33645407140 scopus 로고    scopus 로고
    • note
    • 2 (36% yield, 45% ee), toluene (24% yield, 56% ee), MeCN (38% yield, 48% ee), DMF (34% yield, 21% ee), MeOH (22% yield, 21% ee).
  • 34
    • 33645391499 scopus 로고    scopus 로고
    • note
    • Results of the aza-MBH reaction of 2a with 3a catalyzed by organocatalysts 1d-i in t-BuOMe (0.05 M; substrate concentration of 3a) at -20 °C for 144 h: 1d (no reaction), 1e (71% yield, 88% ee), If (80% yield, 86% ee), 1g (no reaction), 1h (14% yield, 73% ee), 1i (29% yield, 77% ee).
  • 35
    • 33645402963 scopus 로고    scopus 로고
    • note
    • 13C NMR, MS, and IR spectroscopy. Absolute configurations of 5 were determined by comparing the assign of the optical rotations with those in the literature.
  • 36
    • 33645392476 scopus 로고    scopus 로고
    • note
    • The aza-MBH reaction of 2a with 3a was performed in t-BuOMe (0.05M; substrate concentration of 3a) at 0 °C; 6a: no reaction; 6b: (S)-4a, 86 h, 5% yield, 63% ee; 6c: (R)-4a, 48 h, 95% yield, 61% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.