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Volumn 64, Issue 51, 2008, Pages 11697-11705

Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors

Author keywords

1,4 Addition reaction; 4 Methoxytetramates; Pyrrolin 2 ones; Vinylogous Michael reaction

Indexed keywords

LEWIS ACID; PYRROLINE DERIVATIVE;

EID: 55749090628     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.007     Document Type: Article
Times cited : (24)

References (70)
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    • For comprehensive review articles on the chemo- and regiochemical issues and notable applications of the vinylogous aldol-type chemistry, see:
    • For comprehensive review articles on the chemo- and regiochemical issues and notable applications of the vinylogous aldol-type chemistry, see:
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    • In similar reactions involving 2-(trimethylsilyloxy)furans and 3-alkenoyl-1,3-oxazolidin-2-ones, good to excellent diastereo- and enantioselectivity were obtained, by exploiting pyridine bis(oxazoline) (pybox)-lanthanide complexes or binaphthyldiimine-Ni(II) complexes:
    • In similar reactions involving 2-(trimethylsilyloxy)furans and 3-alkenoyl-1,3-oxazolidin-2-ones, good to excellent diastereo- and enantioselectivity were obtained, by exploiting pyridine bis(oxazoline) (pybox)-lanthanide complexes or binaphthyldiimine-Ni(II) complexes:
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    • This reaction was also exploited during the enantioselective synthesis of (+)-compactin; here, a crucial role played by the unsaturated aldehyde acceptor was highlighted in guiding the overall stereoselection of the organocatalyzed process:
    • This reaction was also exploited during the enantioselective synthesis of (+)-compactin; here, a crucial role played by the unsaturated aldehyde acceptor was highlighted in guiding the overall stereoselection of the organocatalyzed process:. Robichaud J., and Trembaly F. Org. Lett. 8 (2006) 597-600
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    • For examples of 'indirect' VMMAR, see:
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    • note
    • During the reaction course, clear evidence of formation of the N-trimethylsilyl adduct from the starting pyrrolinone was observed (TLC, NMR), which returned N-deprotected pyrrolinone under the slightly acidic quenching conditions.
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    • For a comprehensive survey on these topics, see: Noteworthily, the presence of an alkoxy substituent at the C4 position of the ring influences the chemical behavior of the pyrrolinone nucleus, deeply affecting the acidity of the H5-protons, as well as the diverse nucleophilic character at the C3 and C5 carbon atoms. For a comprehensive survey on these topics, see:
    • For a comprehensive survey on these topics, see: Noteworthily, the presence of an alkoxy substituent at the C4 position of the ring influences the chemical behavior of the pyrrolinone nucleus, deeply affecting the acidity of the H5-protons, as well as the diverse nucleophilic character at the C3 and C5 carbon atoms. For a comprehensive survey on these topics, see:. Royles B.J. Chem. Rev. 95 (1995) 1981-2001
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    • Compounds 1c-1e are known substances, which have been nicely exploited in both alkylation and aldol additions/condensations: Li or Na-dienolates:
    • Compounds 1c-1e are known substances, which have been nicely exploited in both alkylation and aldol additions/condensations: Li or Na-dienolates:
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    • For examples of tertiary amine-catalyzed direct aldol reactions, see:
    • For examples of tertiary amine-catalyzed direct aldol reactions, see:
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    • note
    • Addition of 1c to cinnamaldehyde was also tested, with exclusive, low-yielding production of the trimethylsilyl-protected carbinol from 1,2-carbonyl addition attack.
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    • note
    • According to this line of reasoning, complete lack of reactivity between 1c and Z-configured cyclic acceptor 11 could be attributed to the fact that both possible tight transition state models VII and VIII are sterically encumbered and inherently unfavoured.{A figure is presented}


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