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Volumn 43, Issue 15, 2004, Pages 1983-1986

Asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst

Author keywords

Aldol reaction; Amines; Asymmetric catalysis; Tetrazole; Water

Indexed keywords

CHEMICAL REACTIONS; SOLUBILITY;

EID: 2942641357     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352724     Document Type: Article
Times cited : (580)

References (62)
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    • b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352;
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    • For reviews, see: d) B. List, Synlett 2001, 1675;
    • (2001) Synlett , pp. 1675
    • List, B.1
  • 23
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    • For other asymmetric direct aldol reaction, see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
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    • For recent examples of the catalytic direct aldol reactions, see: o) R. Mahrwald, B. Gundogan, J. Am. Chem. Soc. 1998, 120, 413;
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 413
    • Mahrwald, R.1    Gundogan, B.2
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    • a values in water of tetrazoles lie in the range of -0.8 to about 6 depending on the electronic properties of the substituent at position 5 of the tetrazole ring, see: A. A. A. Boraei, J. Chem. Eng. Data 2001, 46, 939.
    • (2001) J. Chem. Eng. Data , vol.46 , pp. 939
    • Boraei, A.A.A.1
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    • note
    • In some respects, our results compare well with the proline-catalyzed reactions.[3] However, what is different from proline is enhanced reactivity leading to a lower catalyst (5-10 mol %) and ketone (1-8 equiv) loading, and even more expanded substrate scope regarding the ketone component. See also the Supporting Information for comparison experiments with proline.
  • 54
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    • After we finished this work, the following important papers were published, which also support our mechanism, see: a) K. Funabiki, N. Honma, W. Hashimoto, M. Matsui, Org. Lett. 2003, 5, 2059;
    • (2003) Org. Lett. , vol.5 , pp. 2059
    • Funabiki, K.1    Honma, N.2    Hashimoto, W.3    Matsui, M.4
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    • note
    • 3CN or MeOD at room temperature for one day.
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    • note
    • The absolute configuration of 4 and 5 was determined by X-ray single-crystal analysis. See the Supporting Information.
  • 58
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    • (Ed.: J. D. Morrison), Academic Press, San Diego
    • a) C. H. Heathcock in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, San Diego, 1984, p. 111.
    • (1984) Asymmetric Synthesis, Vol. 3 , vol.3 , pp. 111
    • Heathcock, C.H.1
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    • note
    • This enantioselective hydroxymethylation is now under investigation with other carbonyl compounds, and the results will appear in a full account.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.