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Volumn 43, Issue 3, 2004, Pages 340-343

Chelation-Controlled Intermolecular Hydroacylation: Direct Addition of Alkyl Aldehydes to Functionalized Alkenes

Author keywords

Aldehydes; Alkenes; Homogeneous catalysis; Hydroacylation; Rhodium

Indexed keywords

ALDEHYDES; ALKYLATION; ESTERS; ETHANE;

EID: 0346500648     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352751     Document Type: Article
Times cited : (132)

References (39)
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    • c) G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1699-1712;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1699-1712
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    • For selected recent examples of catalytic cyclopentanone synthesis, see: a) K. P. Gable, G. A. Benz, Tetrahedron Lett. 1991, 32, 3473-3476;
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3473-3476
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    • d) for an example of intramolecular enantioselective hydroacylation of alkynes, see: K. Tanaka, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 10296-10297.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10296-10297
    • Tanaka, K.1    Fu, G.C.2
  • 16
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    • b) Y. Sato, Y. Oonishi, M. Mori, Angew. Chem. 2002, 114, 1266-1269; Angew. Chem. Int. Ed. 2002, 41, 1218-1221.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1218-1221
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    • For Rh-based systems used in combination with CO or ethylene, see: a) J. Schwartz, J. B. Cannon, J. Am. Chem. Soc. 1974, 96, 4721-4723;
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 4721-4723
    • Schwartz, J.1    Cannon, J.B.2
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    • 0346352848 scopus 로고    scopus 로고
    • note
    • The Co system reported by Brookhart and co-workers[9] employs alkyl aldehydes at moderate temperatures for the hydroacylation of terminal vinyl silanes.
  • 29
    • 0346982711 scopus 로고    scopus 로고
    • note
    • For examples of Rh-catalyzed hydroiminoacylation, see reference [1d] and references therein.
  • 33
    • 0347613697 scopus 로고    scopus 로고
    • note
    • Decarbonylation resulted in stalled reactions and the production of inactive carbonylated catalysts.
  • 36
    • 0347613699 scopus 로고    scopus 로고
    • note
    • For a counterion effect in intramolecular hydroacylation, see reference [6a].
  • 37
    • 0348243491 scopus 로고    scopus 로고
    • note
    • Longer reaction times could also be employed. For example, in the presence of 1.5 mol% of catalyst, 94% conversion was reached at 60°C after 48 h.
  • 38
    • 0347613698 scopus 로고    scopus 로고
    • note
    • 3-(Methylsulfanyl)propanal is available from Sigma-Aldrich Co. Ltd.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.