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Volumn 44, Issue 28, 2005, Pages 4365-4368

Direct catalytic asymmetric mannich-type reactions of N-(2-hydroxyacetyl) pyrrole as an ester-equivalent donor

Author keywords

Amino alcohols; Asymmetric catalysis; Indium; Mannich reaction; Pyrroles

Indexed keywords

CARBOXYLIC ACIDS; CATALYSTS; DERIVATIVES; KETONES;

EID: 22744453251     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501180     Document Type: Article
Times cited : (127)

References (56)
  • 1
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    • A review of the direct Mannich reaction: a) A. Córdova, Acc. Chem. Res. 2004, 37, 102;
    • (2004) Acc. Chem. Res. , vol.37 , pp. 102
    • Córdova, A.1
  • 3
    • 0000119848 scopus 로고    scopus 로고
    • Selected examples of direct Mannich reactions using unmodified ketones and/or aldehydes as donors: with metal catalysts: a) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083;
    • (2001) Angew. Chem. , vol.113 , pp. 3083
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  • 7
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    • with organocatalysts: d) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336
    • List, B.1
  • 16
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    • and references therein. see reviews in ret. [1]
    • k) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356, and references therein. For other related examples, see reviews in ret. [1].
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5356
    • Uraguchi, D.1    Terada, M.2
  • 20
    • 3242721636 scopus 로고    scopus 로고
    • For exceptional examples in Mannich-type reactions using readily enolizable substrates with the oxidation state of carboxylic acid, see: with glycine Schiff base as a donor: a) T. Ooi, M. Kameda, J. Fujii, K. Maruoka, Org. Lett. 2004, 6, 2397;
    • (2004) Org. Lett. , vol.6 , pp. 2397
    • Ooi, T.1    Kameda, M.2    Fujii, J.3    Maruoka, K.4
  • 33
    • 0033606864 scopus 로고    scopus 로고
    • for the application of N-acylpyrrole as a donor after conversion into enol silane, see: b) D. A. Evans, D. S. Johnson, Org. Lett. 1999, 1, 595;
    • (1999) Org. Lett. , vol.1 , pp. 595
    • Evans, D.A.1    Johnson, D.S.2
  • 39
    • 22744458808 scopus 로고    scopus 로고
    • see the Supporting Information
    • For the determination of relative and absolute configurations of Mannich adducts 6a-1, see the Supporting Information.
  • 40
    • 0037420322 scopus 로고    scopus 로고
    • The addition of MS 5 Å had beneficial effects on the reaction rate but did not affect the enantiomeric excess. Similar effects of molecular sieves were observed in related reactions using zinc catalysts and hydroxy ketones as donors; see, a) S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2582
    • Harada, S.1    Kumagai, N.2    Kinoshita, T.3    Matsunaga, S.4    Shibasaki, M.5
  • 44
    • 15944403573 scopus 로고    scopus 로고
    • After submission of this manuscript, an excellent organocatalytic Mannich reaction using α-oxyaldehydes was reported, see: a) I. Ibrahem, A. Córdova, Tetrahedron Lett. 2005, 46, 2839;
    • (2005) Tetrahedron Lett. , vol.46 , pp. 2839
    • Ibrahem, I.1    Córdova, A.2
  • 48
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    • and references therein
    • Angew. Chem. Int. Ed. 2005, 44, 1343, and references therein;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1343
  • 50
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    • in press; see refs [1, 2], and references therein
    • Angew. Chem. Int. Ed. 2005, 44, in press; for other examples using α-oxyke tones, see refs [1, 2], and references therein.
    • (2005) Angew. Chem. Int. Ed. , vol.44
  • 51
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    • note
    • The diastereoselectivity of the reaction with the imine from benzaldehyde was improved by using the bulkier 2,4,6-triisopropylbenzenesulfonyl imine (syn/anti = 78:22, syn: 95% ee); however, reactivity decreased significantly (27% yield).
  • 52
    • 22744434324 scopus 로고    scopus 로고
    • see refs [6, 7], and references therein
    • For conversion of N-acylpyrrole units, see refs [6, 7], and references therein.
  • 56
    • 22744449515 scopus 로고    scopus 로고
    • note
    • 3 can be purchased from Kojundo Chemical lab (sales@kojundo.co.jp).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.