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Volumn 72, Issue 10, 2007, Pages 3949-3951

Synthesis of Z-5-carboxymethylene-1,3-dioxolan-4-ones: A better way

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVE ELIMINATION; TARTARIC ACID; Z-5-CARBOXYMETHYLENE-1,3-DIOXOLAN-4-ONES;

EID: 34248581891     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0700171     Document Type: Article
Times cited : (9)

References (17)
  • 2
    • 34248543473 scopus 로고    scopus 로고
    • Walker, M. A.; Johnson, T. D.; Meanwell, N. A.; Banville, J. Preparation of Carbamoyl Keto Acid Tautomers as HIV Integrase Inhibitors for Treatment of AIDS or ORC. World Patent Appl. 2,001,096,283, 2001; Chem. Abstr. 2002, 136, 53533.
    • Walker, M. A.; Johnson, T. D.; Meanwell, N. A.; Banville, J. Preparation of Carbamoyl Keto Acid Tautomers as HIV Integrase Inhibitors for Treatment of AIDS or ORC. World Patent Appl. 2,001,096,283, 2001; Chem. Abstr. 2002, 136, 53533.
  • 6
    • 37049099484 scopus 로고    scopus 로고
    • In addition to the bromination route outlined in eq 1, compounds in this series have also been prepared by condensation of a glyoxylate ester with a stabilized Wittig reagent: Ramage, R, McCleary, P. P. J. Chem. Soc, Perkin Trans. 1 1984, 1555
    • In addition to the bromination route outlined in eq 1, compounds in this series have also been prepared by condensation of a glyoxylate ester with a stabilized Wittig reagent: Ramage, R.; McCleary, P. P. J. Chem. Soc., Perkin Trans. 1 1984, 1555.
  • 7
    • 13444287979 scopus 로고    scopus 로고
    • For a thought-provoking discussion regarding the impact of the oxidation state of intermediates on synthetic efficiency, see: Fraunhoffer, K. J, Bachovchin, D. A, White, M. C. Org. Lett. 2005, 7, 223
    • For a thought-provoking discussion regarding the impact of the oxidation state of intermediates on synthetic efficiency, see: Fraunhoffer, K. J.; Bachovchin, D. A.; White, M. C. Org. Lett. 2005, 7, 223.
  • 11
    • 34248557726 scopus 로고    scopus 로고
    • Chem. Abstr. 1973, 78, 3643.
    • Chem. Abstr. 1973, 78, 3643.
  • 13
    • 34248504712 scopus 로고    scopus 로고
    • Quenching the reaction mixture with DCl resulted in no deuterium incorporation in the recovered 3. This seems to rule out the possibility that deprotonation occurs but results in a chelation-stabilized carbanion that does not undergo elimination.
    • Quenching the reaction mixture with DCl resulted in no deuterium incorporation in the recovered 3. This seems to rule out the possibility that deprotonation occurs but results in a chelation-stabilized carbanion that does not undergo elimination.
  • 14
    • 0022858494 scopus 로고    scopus 로고
    • For another example utilizing sodium bicarbonate in the alkylation of a base-sensitive carboxylic acid, see: Mobashery, S, Johnston, M. J. Org. Chem. 1986, 51, 4723
    • For another example utilizing sodium bicarbonate in the alkylation of a base-sensitive carboxylic acid, see: Mobashery, S.; Johnston, M. J. Org. Chem. 1986, 51, 4723.
  • 16
    • 33751176464 scopus 로고    scopus 로고
    • For a somewhat related transformation, see
    • For a somewhat related transformation, see: Smith, B. M.; Graham, A. E. Tetrahedron Lett. 2006, 47, 9317.
    • (2006) Tetrahedron Lett , vol.47 , pp. 9317
    • Smith, B.M.1    Graham, A.E.2
  • 17
    • 34248541116 scopus 로고    scopus 로고
    • The slightly lower ee for the (S)-acetal presumably reflects the somewhat lower optical purity of the unnatural (S,S)-tartaric acid starting material.
    • The slightly lower ee for the (S)-acetal presumably reflects the somewhat lower optical purity of the unnatural (S,S)-tartaric acid starting material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.