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Volumn 72, Issue 14, 2007, Pages 5457-5460

Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNES; METHYLIMIDAZOLES; REACTION CONDITIONS;

EID: 34447335324     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0707535     Document Type: Article
Times cited : (76)

References (64)
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    • The use of stoichiometric amounts of chiral amino alcohol-based ligands: (a) Jiang, B.; Chen, Z. L.; Xiong, W. N. Chem. Commun. 2002, 1524.
    • The use of stoichiometric amounts of chiral amino alcohol-based ligands: (a) Jiang, B.; Chen, Z. L.; Xiong, W. N. Chem. Commun. 2002, 1524.
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    • Bisoxazolidine-catalyzed enantioselective alkynylation of aromatic aldehydes at low temperature (-4 to -15°C): Wolf, C.; Liu, S. J. Am. Chem. Soc. 2006, 128, 10996.
    • Bisoxazolidine-catalyzed enantioselective alkynylation of aromatic aldehydes at low temperature (-4 to -15°C): Wolf, C.; Liu, S. J. Am. Chem. Soc. 2006, 128, 10996.
  • 19
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    • Catalytic procedures based on amino alcohol ligands focus on the addition of phenylacetylene to aromatic aldehydes, while few address the need to utilize functional alkynes: (a) Xu, Z, Wang, R, Xu, J, Da, C, Yan, W, Chen, C. Angew. Chem, Int. Ed. 2003, 42, 5747
    • Catalytic procedures based on amino alcohol ligands focus on the addition of phenylacetylene to aromatic aldehydes, while few address the need to utilize functional alkynes: (a) Xu, Z.; Wang, R.; Xu, J.; Da, C.; Yan, W.; Chen, C. Angew. Chem., Int. Ed. 2003, 42, 5747.
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    • Dinuclear Zn-catalyzed asymmetric alkynylation of α,β- unsaturated aldehydes at 4°C: Trost, B. M.; Weiss, A. H.; von Wangelin, A. J. J. Am. Chem. Soc. 2006, 128, 8.
    • Dinuclear Zn-catalyzed asymmetric alkynylation of α,β- unsaturated aldehydes at 4°C: Trost, B. M.; Weiss, A. H.; von Wangelin, A. J. J. Am. Chem. Soc. 2006, 128, 8.
  • 24
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    • Selected examples for modified BINOLs as ligands: (a) Moore, D.; Huang, W. S.; Xu, M. H.; Pu, L. Tetrahedron Lett. 2002, 43, 8831.
    • Selected examples for modified BINOLs as ligands: (a) Moore, D.; Huang, W. S.; Xu, M. H.; Pu, L. Tetrahedron Lett. 2002, 43, 8831.
  • 33
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    • The method also required 1 equiv of an additional chiral sulfonamide ligand and was only applied in the addition of phenylacetylene to aromatic aldehydes below 0°C for 1-2 days: Li, X. S.; Lu, G.; Kwok, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 2002, 124, 12636.
    • The method also required 1 equiv of an additional chiral sulfonamide ligand and was only applied in the addition of phenylacetylene to aromatic aldehydes below 0°C for 1-2 days: Li, X. S.; Lu, G.; Kwok, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 2002, 124, 12636.
  • 37
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    • In this regard, one impressive example has been illustrated by the recent studies of the Carreira group, in which a catalytic version of the addition procedure could be conducted at elevated temperatures, i.e, 60°C, to overcome the kinetic barrier inhibiting protonation of the first formed Zn-alkoxide, avoiding the use of stoichiometric quantities of Zn(OTf) 2 and N-methylephedrine. See ref 3b
    • 2 and N-methylephedrine. See ref 3b.
  • 38
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    • For reviews on the concept of dual acid/base catalysis, see: a
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    • (2001) Chem. - Eur. J , vol.7 , pp. 5247
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    • Takita, R, Fukuta, Y, Tsuji, R, Ohshima, T, Shibasaki, M. Org. Lett. 2005, 7, 3849. Also see ref 15
    • Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 3849. Also see ref 15.
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    • Trost, B. M, Fleming, I, Eds, Pergamon Press: New York
    • (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 521.
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  • 59
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    • There was not any information describing the asymmetric addition of trimethylsilylacetylene to aldehydes in the BINOL-Ti(OiPr) 4-HMPA-Et2Zn as previously reported by Pu and co-workers. See ref 11
    • 2Zn as previously reported by Pu and co-workers. See ref 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.