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Volumn 71, Issue 2, 2006, Pages 840-843

Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM COMPOUNDS; CATALYSIS; CATALYST SELECTIVITY; CHELATION; NITROGEN COMPOUNDS; STEREOCHEMISTRY;

EID: 30744473984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052121t     Document Type: Article
Times cited : (49)

References (50)
  • 12
    • 30744447423 scopus 로고    scopus 로고
    • note
    • The MPV reduction was generally not considered In give good diastereaselectivities. See ref 2u.
  • 13
    • 33750111587 scopus 로고
    • (a) Lund, H. Ber, 1937, 70B, 1520.
    • (1937) Ber , vol.70 B , pp. 1520
    • Lund, H.1
  • 19
    • 30744478621 scopus 로고    scopus 로고
    • EP 703209, 1996
    • (g) Hilpert, H. EP 703209, 1996.
    • Hilpert, H.1
  • 34
    • 30744434595 scopus 로고    scopus 로고
    • note
    • Unlike many other ketones in Table 2, the product isomers 3a/5a are readily separated by LC for easy analysis during screening.
  • 36
    • 30744454766 scopus 로고    scopus 로고
    • note
    • N-H of the carbamate on 2n provides the third equiv of a proton to fully quench DIBAL's two isobutyl groups and one hydride.
  • 37
    • 33947300580 scopus 로고
    • 3 without IPA was very sluggish, It has been proposed that IPA can help convert the tetramer of aluminum isopropoxide to the much more reactive form (∼2.8 oligomer). Shiner, V. J.; Whiltaker, D. J. Am. Chem. Sac. 1969, 91, 394.
    • (1969) J. Am. Chem. Sac. , vol.91 , pp. 394
    • Shiner, V.J.1    Whiltaker, D.2
  • 38
    • 30744446914 scopus 로고    scopus 로고
    • note
    • 3, suggesting the deactivation of the catalyst to a less active form during the reaction.
  • 39
    • 30744467892 scopus 로고    scopus 로고
    • note
    • It was found that addition of a catalytic amount of bipyridine resulted in a slower MPV reduction.
  • 42
    • 30744466112 scopus 로고    scopus 로고
    • note
    • We also observed about the same d.r. at 3 h (∼60% conv) as that at 18 h for the MPV reduction of 2a.
  • 49
    • 30744435295 scopus 로고    scopus 로고
    • note
    • 4 gave an anti/syn selectivity of 94:6.
  • 50
    • 30744451125 scopus 로고    scopus 로고
    • note
    • Direct MPV reduction on 2-(ethylamino)propiophenone hydrochloride to give 19/20 was unsuccessful possibly because of the reaction between the amino group and the ketone.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.