메뉴 건너뛰기




Volumn 130, Issue 52, 2008, Pages 17961-17969

Three-component Ag-catalyzed enantioselective vinylogous mannich and aza-diels - Alder reactions with alkyl-substituted aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; ALKYNYL; ARYL UNITS; CATALYST CONTROL; CHIRAL LIGAND; DIASTEREOMER; DIASTEREOMERS; DIELS-ALDER REACTION; ENANTIOSELECTIVE; HETEROATOM; HIGH EFFICIENCY; METHOXYANILINE; THREE-COMPONENT;

EID: 58849106756     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807243t     Document Type: Article
Times cited : (127)

References (61)
  • 1
    • 67849124304 scopus 로고    scopus 로고
    • For a recent review of Mannich reactions involving aldimines, see
    • For a recent review of Mannich reactions involving aldimines, see:
  • 2
    • 1642415515 scopus 로고    scopus 로고
    • For select recent reports of catalytic enantioselective Mannich reactions (not VM) involving aldimines, see
    • (a) Córdova, A. Acc. Chem. Res. 2004, 37, 102-112. For select recent reports of catalytic enantioselective Mannich reactions (not VM) involving aldimines, see:
    • (2004) Acc. Chem. Res , vol.37 , pp. 102-112
    • Córdova, A.1
  • 10
    • 67849116857 scopus 로고    scopus 로고
    • For an overview regarding applications of Mannich reactions to the preparation of biologically active molecules and target-oriented synthesis, see
    • For an overview regarding applications of Mannich reactions to the preparation of biologically active molecules and target-oriented synthesis, see:
  • 13
    • 40149096195 scopus 로고    scopus 로고
    • For an overview of utility of chiral Ag-based phosphine complexes in enantioselective reactions, see
    • For an overview of utility of chiral Ag-based phosphine complexes in enantioselective reactions, see: Yanagisawa, A.; Arai, T. Chem. Commun. 2008, 1165-1172.
    • (2008) Chem. Commun , pp. 1165-1172
    • Yanagisawa, A.1    Arai, T.2
  • 14
    • 51049115331 scopus 로고    scopus 로고
    • For a review of Ag-catalyzed enantioselective reactions, see
    • For a review of Ag-catalyzed enantioselective reactions, see: Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132-3148.
    • (2008) Chem. Rev , vol.108 , pp. 3132-3148
    • Naodovic, M.1    Yamamoto, H.2
  • 19
    • 67849103721 scopus 로고    scopus 로고
    • For disclosures regarding catalytic enantioselective VM reactions that include examples of alkyl-substituted aldimines, see: With i-Pr- and Cy-substituted aldimines
    • For disclosures regarding catalytic enantioselective VM reactions that include examples of alkyl-substituted aldimines, see: With i-Pr- and Cy-substituted aldimines:
  • 20
    • 53549088683 scopus 로고    scopus 로고
    • With two closely related n-alkyl-substituted aldimines
    • (a) Akiyama, T.; Honma, Y.; Itoh, J.; Fuchibe, K. Adv. Synth Catal. 2008, 350, 399-402. With two closely related n-alkyl-substituted aldimines:
    • (2008) Adv. Synth Catal , vol.350 , pp. 399-402
    • Akiyama, T.1    Honma, Y.2    Itoh, J.3    Fuchibe, K.4
  • 23
    • 67849094230 scopus 로고    scopus 로고
    • For reports on catalytic enantioselective aza-Diels-Alder reactions that include examples with alkyl-substituted aldimines, see: With only Cysubstituted aldimines
    • For reports on catalytic enantioselective aza-Diels-Alder reactions that include examples with alkyl-substituted aldimines, see: With only Cysubstituted aldimines:
  • 27
    • 23744473863 scopus 로고    scopus 로고
    • For a related catalytic enantioselective aza-Diels-Alder protocol, see: d
    • For a related catalytic enantioselective aza-Diels-Alder protocol, see: (d) Sunden, H.; Ibrahem, I.; Eriksson, L.; Córdova, A. Angew. Chem., Int. Ed. 2005, 44, 4877-4880.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 4877-4880
    • Sunden, H.1    Ibrahem, I.2    Eriksson, L.3    Córdova, A.4
  • 28
    • 0034734313 scopus 로고    scopus 로고
    • For catalytic enantioselective Mannich-type reactions (not VM or aza-Diels-Alder) that include reactions of alkyl-substituted aldimines, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180-8186.
    • For catalytic enantioselective Mannich-type reactions (not VM or aza-Diels-Alder) that include reactions of alkyl-substituted aldimines, see: (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180-8186.
  • 37
    • 0030788354 scopus 로고    scopus 로고
    • For use of a related N-arylimine in Zr-catalyzed Mannich reactions with silylketene acetals, see
    • For use of a related N-arylimine in Zr-catalyzed Mannich reactions with silylketene acetals, see: Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 7153-7154
    • Ishitani, H.1    Ueno, M.2    Kobayashi, S.3
  • 39
    • 67849097315 scopus 로고    scopus 로고
    • To the best of our knowledge, there is only one reported example of a catalytic enantioselective Mannich reaction that involves a hetero-atom- containing imine benzyloxy acetaldehyde-derived imine, see ref 10b
    • To the best of our knowledge, there is only one reported example of a catalytic enantioselective Mannich reaction that involves a hetero-atom- containing imine (benzyloxy acetaldehyde-derived imine); see ref 10b.
  • 40
    • 67849090521 scopus 로고    scopus 로고
    • See the Supporting Information for details of ligand screening studies
    • See the Supporting Information for details of ligand screening studies.
  • 41
    • 0347129770 scopus 로고    scopus 로고
    • For a case involving an enantioselective conjugate addition of an enantiomerically enriched enone with a stereogenic center a to the reacting site, where use of an amino acid-based chiral phosphine catalyst results in enhancement of selectivity, see: (a) Cesati, R. R, de Armas, J, Hoveyda, A. H. J. Am.Chem. Soc. 2004, 126, 96-101. For an example where an enantioselective alkylation of an enantiomerically enriched allylic phosphate promoted by amino acid-based catalyst proceeds readily and selectively with only one of the substrate enantiomers, see
    • For a case involving an enantioselective conjugate addition of an enantiomerically enriched enone with a stereogenic center a to the reacting site, where use of an amino acid-based chiral phosphine catalyst results in enhancement of selectivity, see: (a) Cesati, R. R.; de Armas, J.; Hoveyda, A. H. J. Am.Chem. Soc. 2004, 126, 96-101. For an example where an enantioselective alkylation of an enantiomerically enriched allylic phosphate promoted by amino acid-based catalyst proceeds readily and selectively with only one of the substrate enantiomers, see:
  • 43
    • 67849128673 scopus 로고    scopus 로고
    • See the Supporting Information for details regarding the preparation and enantiomeric purity of chiral non-racemic aldehydes used in this study. The selectivity values shown in Table 4 are corrected
    • See the Supporting Information for details regarding the preparation and enantiomeric purity of chiral non-racemic aldehydes used in this study. The selectivity values shown in Table 4 are corrected.
  • 45
    • 67849104610 scopus 로고    scopus 로고
    • For accuracy in measuring small amounts of chiral ligand and Ag salt, transformations were performed in the presence of 5 mol % catalyst.
    • For accuracy in measuring small amounts of chiral ligand and Ag salt, transformations were performed in the presence of 5 mol % catalyst.
  • 46
    • 67849116858 scopus 로고    scopus 로고
    • Although the gram scale reaction shown in eq 1 was performed with 5 mol, catalyst, previous studies involving related Mannich-type processes indicate that lower catalyst loadings can be readily extended to larger scale transformations; for example, see ref 5
    • Although the gram scale reaction shown in eq 1 was performed with 5 mol % catalyst, previous studies involving related Mannich-type processes indicate that lower catalyst loadings can be readily extended to larger scale transformations; for example, see ref 5.
  • 48
    • 84869573696 scopus 로고    scopus 로고
    • As illustrated by the examples below, enantioselective VM reactions with aldimines derived from α,β-unsaturated aldehydes proceed to >98% conversion and in high diastereo- and enantioselectivity but in low yields. Control experiments point to product instability.
    • As illustrated by the examples below, enantioselective VM reactions with aldimines derived from α,β-unsaturated aldehydes proceed to >98% conversion and in high diastereo- and enantioselectivity but in low yields. Control experiments point to product instability.
  • 49
    • 67849111523 scopus 로고    scopus 로고
    • For other related examples of catalytic enantioselective additions promoted by this class of amino acid-based chiral ligands, see
    • For other related examples of catalytic enantioselective additions promoted by this class of amino acid-based chiral ligands, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.