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Volumn 15, Issue 5, 2011, Pages 1052-1062

Use of an iridium-catalyzed redox-neutral alcohol-amine coupling on kilogram scale for the synthesis of a GlyT1 inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINES; CATALYST LOADINGS; ENVIRONMENTALLY FRIENDLY SYNTHESIS; TERTIARY AMINE;

EID: 80053015358     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200174k     Document Type: Article
Times cited : (95)

References (29)
  • 6
    • 0003154786 scopus 로고    scopus 로고
    • Brighty, K.; Castaldi, M. Synlett 1996, 1097-1099. We utilized a different route to prepare 2 to facilitate safe execution on scale. See the Supporting Information
    • (1996) Synlett , pp. 1097-1099
    • Brighty, K.1    Castaldi, M.2
  • 7
    • 79957698619 scopus 로고    scopus 로고
    • A recent report (Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451-3479) analyzing the types of reactions utilized in current medicinal chemistry publications has found that ca. 65% of all transformations are bond-forming processes, and of those, over 80% are C-N bond-forming reactions, with C-C bond-forming reactions a distant second at 15%. In the direct experience of this author this trend toward late-stage fragment assembly through carbon-heteroatom coupling reactions has become much more prevalent over the past decade
    • (2011) J. Med. Chem. , vol.54 , pp. 3451-3479
    • Roughley, S.D.1    Jordan, A.M.2
  • 10
    • 0028785752 scopus 로고
    • For an example of a reaction where debenzylation proceeds in the presence of formaldehyde, see: Kende, A. S.; Liu, K.; Brands, K. M. J. J. Am. Chem. Soc. 1995, 117, 10597-10598. It appears that increased catalyst loading is necessary to retain catalytic activity
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10597-10598
    • Kende, A.S.1    Liu, K.2    Brands, K.M.J.3
  • 20
    • 72649096505 scopus 로고    scopus 로고
    • and references therein
    • Krische and co-workers have postulated that deprotonation of an iridium(III) hydride by a carbonate base resulting in formation of an iridium(I) species is a key step in the enantioselective coupling between alcohols and allyl nucleophiles. See: Han, S. B.; Kim, I. S.; Krische, M. J. Chem. Commun. 2009, 7278 and references therein
    • (2009) Chem. Commun. , pp. 7278
    • Han, S.B.1    Kim, I.S.2    Krische, M.J.3
  • 29
    • 77949814122 scopus 로고    scopus 로고
    • 2-catalyzed amination of sulfonamides with alcohols, which also proceeds with a catalyst loading of 0.05 mol % Ir. The increased acidity of the sulfonamide is responsible for this catalytic activity and a strong base (KO t -Bu) has been identified to be necessary to facilitate turnover. See: Zhu, M.; Fujita, K.; Yamaguchi, R. Org. Lett. 2010, 12, 1336-1339
    • (2010) Org. Lett. , vol.12 , pp. 1336-1339
    • Zhu, M.1    Fujita, K.2    Yamaguchi, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.