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Volumn 47, Issue 25, 2008, Pages 4632-4634

Organocatalytic reactions with acetaldehyde

Author keywords

Acetaldehyde; Asymmetric synthesis; C C coupling; Natural products; Synthetic methods

Indexed keywords

CARBONYLATION; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; COMPLEXATION; REACTION KINETICS; STEREOCHEMISTRY;

EID: 53349153675     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801231     Document Type: Short Survey
Times cited : (79)

References (38)
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    • For selected reviews, see: a
    • For selected reviews, see: a) C. F. Barbas III, Angew. Chem. 2008, 120, 44;
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    • Barbas III, C.F.1
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    • thematic issue: Organocatalysis
    • b) Chem. Rev. 2007, 107, 5413-5883 (thematic issue: Organocatalysis);
    • (2007) Chem. Rev , vol.107 , pp. 5413-5883
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    • thematic issue: Organocatalysis in Organic Synthesis
    • e) Tetrahedron 2006, 62, 243-502 (thematic issue: Organocatalysis in Organic Synthesis);
    • (2006) Tetrahedron , vol.62 , pp. 243-502
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    • 14744286984 scopus 로고    scopus 로고
    • thematic issue: Organic Catalysis
    • i) Adv. Synth. Catal. 2004, 346, 1007-1249 (thematic issue: Organic Catalysis);
    • (2004) Adv. Synth. Catal , vol.346 , pp. 1007-1249
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    • thematic issue: Asymmetric Organocatalysis
    • j) Acc. Chem. Res. 2004, 37, 487-631 (thematic issue: Asymmetric Organocatalysis);
    • (2004) Acc. Chem. Res , vol.37 , pp. 487-631
  • 19
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    • The reports on asymmetric organocatalysis have been growing exponentially even when normalized against the general growth in all scientific publications
    • The reports on asymmetric organocatalysis have been growing exponentially even when normalized against the general growth in all scientific publications.
  • 20
    • 84891546770 scopus 로고    scopus 로고
    • Curiously, long before the explosion of organocatalysis, acetaldehyde itself may be considered one of the first compounds used as an organocatalyst: J. von Liebig, Justus Liebigs Ann. Chem. 1860, 113, 246.
    • Curiously, long before the explosion of organocatalysis, acetaldehyde itself may be considered one of the first compounds used as an organocatalyst: J. von Liebig, Justus Liebigs Ann. Chem. 1860, 113, 246.
  • 21
    • 34547178959 scopus 로고    scopus 로고
    • For the employment of acetaldehyde as a nucleophile in aldolase-catalyzed reactions, see: a
    • For the employment of acetaldehyde as a nucleophile in aldolase-catalyzed reactions, see: a) S. M. Dean, W. A. Greenberg, C.-H. Wong, Adv. Synth. Catal. 2007, 349, 1308;
    • (2007) Adv. Synth. Catal , vol.349 , pp. 1308
    • Dean, S.M.1    Greenberg, W.A.2    Wong, C.-H.3
  • 24
    • 0035921177 scopus 로고    scopus 로고
    • For the employment of acetaldehyde as a nucleophile in thiamine-catalyzed reactions, see: c
    • For the employment of acetaldehyde as a nucleophile in thiamine-catalyzed reactions, see: c) G. Goetz, P. Iwan, B. Hauer, M. Breuer, M. Pohl, Biotechnol. Bioeng. 2001, 74, 317.
    • (2001) Biotechnol. Bioeng , vol.74 , pp. 317
    • Goetz, G.1    Iwan, P.2    Hauer, B.3    Breuer, M.4    Pohl, M.5
  • 29
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    • For a review, see
    • For a review, see: C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
    • (2006) Angew. Chem , vol.118 , pp. 8042
    • Palomo, C.1    Mielgo, A.2
  • 31
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    • The configuration of the product is imposed by the bulkiness of the substituent α to the pyrrolidine nitrogen atom, forcing the attack of the electrophile to the lower face of the enamine. Thus, the configuration of the final adducts is opposite to that for the L-proline-catalyzed reactions
    • The configuration of the product is imposed by the bulkiness of the substituent α to the pyrrolidine nitrogen atom, forcing the attack of the electrophile to the lower face of the enamine. Thus, the configuration of the final adducts is opposite to that for the L-proline-catalyzed reactions.
  • 34
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    • It should be mentioned that the enantioselectivity of the L-proline catalyzed Mannich reaction is opposite to that of the sterochemistry observed for the corresponding L-proline catalyzed aldol reaction
    • It should be mentioned that the enantioselectivity of the L-proline catalyzed Mannich reaction is opposite to that of the sterochemistry observed for the corresponding L-proline catalyzed aldol reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.