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Volumn 12, Issue 20, 2010, Pages 4494-4497

Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINONE DERIVATIVE; TETRAHYDROPYRIMIDINONE; UREA;

EID: 77957826125     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101755m     Document Type: Article
Times cited : (61)

References (47)
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    • For examples of bioactive 1,3-amines of natural or synthetic origin, see
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    • For examples, see
    • For examples, see
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    • For a recent review on chiral amine synthesis, see
    • For a recent review on chiral amine synthesis, see: Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753
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    • For previous work from our group on direct stereoselective amine synthesis, see
    • For previous work from our group on direct stereoselective amine synthesis, see
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    • For reviews on allylic substitution reactions, see
    • For reviews on allylic substitution reactions, see
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    • For examples of syntheses of nitrogen-containing heterocycles by intramolecular allylic substitutions, see
    • For examples of syntheses of nitrogen-containing heterocycles by intramolecular allylic substitutions, see
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    • 3, LHMDS, DBU, proton sponge) and less electron-deficient isocyanates resulted in lower degrees of conversion.
    • 3, LHMDS, DBU, proton sponge) and less electron-deficient isocyanates resulted in lower degrees of conversion.
  • 37
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    • For recent related amination reactions with urea substrates, see ref 9h and
    • For recent related amination reactions with urea substrates, see ref 9h and: Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707
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    • For an amination reaction using a tosyl amide, see
    • For an amination reaction using a tosyl amide, see: Yin, G.; Wu, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 11978
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11978
    • Yin, G.1    Wu, Y.2    Liu, G.3
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    • In all cases, stereochemical assignment was based on NMR methods, e.g.
    • In all cases, stereochemical assignment was based on NMR methods, e.g.
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    • Potentially, this pronounced solvent effect may be rationalized by a reversal of the enantiofacial bias of the allylic substitution reaction. Presumably, in THF a conventional attack of the nucleophile on the side opposite to the π-allyl complex is expected, leading to an inversion at the configuration of the respective carbon center. In contrast to THF, the nucleophilic amide should be much less solvated in DCM. Possibly, the nucleophile may then directly attack the π-allyl intermediate on the same side as the cationic π-allyl complex, based on attractive charge - charge interactions. This would then lead to retention of the configuration.
    • Potentially, this pronounced solvent effect may be rationalized by a reversal of the enantiofacial bias of the allylic substitution reaction. Presumably, in THF a conventional attack of the nucleophile on the side opposite to the π-allyl complex is expected, leading to an inversion at the configuration of the respective carbon center. In contrast to THF, the nucleophilic amide should be much less solvated in DCM. Possibly, the nucleophile may then directly attack the π-allyl intermediate on the same side as the cationic π-allyl complex, based on attractive charge - charge interactions. This would then lead to retention of the configuration.
  • 41
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    • For a recent mechanistic study with "hard" and "soft" nucleophiles in allylic substitution reactions, see
    • For a recent mechanistic study with "hard" and "soft" nucleophiles in allylic substitution reactions, see: Shintani, R.; Tsuji, T.; Park, S.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 7508
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    • All required urea substrates (10a - f) were readily prepared by four-component coupling, in analogy to Scheme 2, by using either the method of Tian (ref 10) or
    • All required urea substrates (10a - f) were readily prepared by four-component coupling, in analogy to Scheme 2, by using either the method of Tian (ref 10) or: Phukan, P. J. Org. Chem. 2004, 69, 4005
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    • For full details: see Supporting Information.
    • For full details: see Supporting Information.
  • 47
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    • In contrast, efforts to remove the urea under similar conditions at the stage of 11 or 12 resulted in only low degrees of conversion.
    • In contrast, efforts to remove the urea under similar conditions at the stage of 11 or 12 resulted in only low degrees of conversion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.