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Volumn , Issue 12, 1997, Pages 2409-2418

Diastereoselective protonation of chiral enolates with chelating proton donors under reagent control: Scope, mechanism, and applications

Author keywords

Cuprates; Enolates; Metalations; Protonations; Stereoselectivity

Indexed keywords


EID: 33749005694     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719971204     Document Type: Review
Times cited : (57)

References (91)
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    • The formation of enolate-amine complexes is utilized in enantioselective protonations by "Lewis-acid induced internal proton transfer": [16a] E. Vedejs, N. Lee, J. Am. Chem. Soc. 1995, 117, 891-900, and references cited therein.
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    • Another consequence of the amine effect is the observation of low degrees of deuterium incorporation when enolates prepared from LDA are treated with deuterated proton sources: [17a] P. L. Creger, J. Am. Chem. Soc. 1970, 92, 1396-1397.
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    • Similarly, the protonation of the magnesium enolate formed by Cul-catalyzed 1,4-addition of MeMgBr to enone 1 with ethyl salicylate gave a product ratio of cis-3:trans-3 = 38:62
    • Similarly, the protonation of the magnesium enolate formed by Cul-catalyzed 1,4-addition of MeMgBr to enone 1 with ethyl salicylate gave a product ratio of cis-3:trans-3 = 38:62.
  • 61
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    • cis:trans ratios for the protonation of enolate 2 with different salicylates: phenyl salicylate: 89:11; (1′R)-menthyl salicylate: 91:9; (1′S)-menthyl salicylate: 93:7; t-butyl salicylate: 94:6; methyl salicylate: 96:4; ethyl salicylate: 96:4
    • cis:trans ratios for the protonation of enolate 2 with different salicylates: phenyl salicylate: 89:11; (1′R)-menthyl salicylate: 91:9; (1′S)-menthyl salicylate: 93:7; t-butyl salicylate: 94:6; methyl salicylate: 96:4; ethyl salicylate: 96:4.
  • 62
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    • cis:trans ratio for the protonation of enolate 2 with 2-methoxyphenol: 70:30; with methyl 8-hydroxy-1-naphthoate: 40:60.
    • cis:trans ratio for the protonation of enolate 2 with 2-methoxyphenol: 70:30; with methyl 8-hydroxy-1-naphthoate: 40:60.
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    • Like-unlike nomenclature
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    • The use of palladium on charcoal as hydrogenation catalyst caused considerable epimerization at C-2 to give large amounts of trans-3
    • The use of palladium on charcoal as hydrogenation catalyst caused considerable epimerization at C-2 to give large amounts of trans-3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.