메뉴 건너뛰기




Volumn 47, Issue 15, 2008, Pages 2876-2879

Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature

Author keywords

Amides; Boronic acids; Carboxylic acids; Cycloaddition; Organocatalysis

Indexed keywords

AMINES; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; KETONES; ORGANIC ACIDS; ORGANIC COMPOUNDS;

EID: 42249107680     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705468     Document Type: Article
Times cited : (365)

References (35)
  • 15
    • 0001659674 scopus 로고    scopus 로고
    • Molecular sieves were shown to catalyze amidations at very high temperatures: J. Cossy, C. Pale-Grosdemange, Tetrahedron Lett. 1989, 30, 2771-2774. No such effect was observed under our reaction conditions.
    • Molecular sieves were shown to catalyze amidations at very high temperatures: J. Cossy, C. Pale-Grosdemange, Tetrahedron Lett. 1989, 30, 2771-2774. No such effect was observed under our reaction conditions.
  • 16
    • 33751568118 scopus 로고    scopus 로고
    • Catalyst 2 was synthesized based on a procedure by Scott and co-workers: H. A. Wegner, H. Reisch, K. Rauch, A. Demeter, K. A. Zachariasse, A. de Meijere, L. T. Scott, J. Org. Chem. 2006, 71, 9080-9087. See detailed procedure in Supporting Information.
    • Catalyst 2 was synthesized based on a procedure by Scott and co-workers: H. A. Wegner, H. Reisch, K. Rauch, A. Demeter, K. A. Zachariasse, A. de Meijere, L. T. Scott, J. Org. Chem. 2006, 71, 9080-9087. See detailed procedure in Supporting Information.
  • 23
    • 53549130137 scopus 로고    scopus 로고
    • The use of previously reported conditions (toluene, heating at reflux)[7] led to greater than 30% racemization
    • [7] led to greater than 30% racemization.
  • 24
    • 53549126509 scopus 로고    scopus 로고
    • [10] Further, we observed no formation of acetic anhydride when acetic acid and 2 are mixed alone under the same amidation conditions as in Table 1. Moreover, in the same conditions, butyric anhydride reacted efficiently with N-methylbenzylamine, a substrate that failed by direct amidation catalyzed by 2.
    • [10] Further, we observed no formation of acetic anhydride when acetic acid and 2 are mixed alone under the same amidation conditions as in Table 1. Moreover, in the same conditions, butyric anhydride reacted efficiently with N-methylbenzylamine, a substrate that failed by direct amidation catalyzed by 2.
  • 26
    • 53549123148 scopus 로고    scopus 로고
    • 2 8.8) and thus cannot explain its exceptional catalytic activity.
    • 2 8.8) and thus cannot explain its exceptional catalytic activity.
  • 28
    • 33947450628 scopus 로고    scopus 로고
    • For example, the Diels-Alder reactions between acrylic acid and cyclopentadiene and furan require, respectively, one hour at 165°C and 75 days at 35°C to achieve reasonable yields of products: a F. X. Werber, J. E. Jansen, T. L. Gresham, J. Am. Chem. Soc. 1952, 74, 532-535;
    • For example, the Diels-Alder reactions between acrylic acid and cyclopentadiene and furan require, respectively, one hour at 165°C and 75 days at 35°C to achieve reasonable yields of products: a) F. X. Werber, J. E. Jansen, T. L. Gresham, J. Am. Chem. Soc. 1952, 74, 532-535;
  • 30
    • 53549104555 scopus 로고    scopus 로고
    • Phenylboronic acid gave only 25% yield under the same conditions
    • Phenylboronic acid gave only 25% yield under the same conditions.
  • 31
    • 53549132978 scopus 로고    scopus 로고
    • Contrary to amidations where attack of the amine regenerates the catalyst (Scheme 3A), a small amount of water (from condensation of the acid and the catalyst) is required to regenerate the catalyst from the cycloadduct.
    • Contrary to amidations where attack of the amine regenerates the catalyst (Scheme 3A), a small amount of water (from condensation of the acid and the catalyst) is required to regenerate the catalyst from the cycloadduct.
  • 34
    • 34347335758 scopus 로고    scopus 로고
    • For an excellent essay on cascade catalysis, see
    • For an excellent essay on cascade catalysis, see: A. M. Walji, D.W. C. MacMillan, Synlett 2007, 1477-1489.
    • (2007) Synlett , pp. 1477-1489
    • Walji, A.M.1    MacMillan, D.W.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.