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Volumn 72, Issue 6, 2007, Pages 2040-2045

Nitrile biotransformations for the efficient synthesis of highly enantiopure 1-arylaziridine-2-carboxylic acid derivatives and their stereoselective ring-opening reactions

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; DERIVATIVES; REACTION KINETICS; REGIOSELECTIVITY; STEREOSELECTIVITY;

EID: 33947279549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062339v     Document Type: Article
Times cited : (54)

References (80)
  • 1
    • 77951231590 scopus 로고    scopus 로고
    • For a recent monograph, see: Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: New York, 2006. For recent reviews, see:
    • (a) For a recent monograph, see: Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: New York, 2006. For recent reviews, see:
  • 3
    • 33747120694 scopus 로고    scopus 로고
    • (c) Xu, X. E. Tetrahedron 2004, 60, 2701.
    • (2004) Tetrahedron , vol.60 , pp. 2701
    • Xu, X.E.1
  • 11
    • 84890989114 scopus 로고    scopus 로고
    • Aziridine natural products - discovery, biological activity, and biosynthesis
    • For aziridine natural products, see:, Yudin, A. K, Ed, Wiley-VCH: New York, Chapter 11
    • (a) For aziridine natural products, see: Lowden, P. P. Aziridine natural products - discovery, biological activity, and biosynthesis. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: New York, 2006; Chapter 11.
    • (2006) Aziridines and Epoxides in Organic Synthesis
    • Lowden, P.P.1
  • 12
    • 84891034662 scopus 로고    scopus 로고
    • Asymmetric syntheses with aziridinecarboxylate and aziridinephosphonate building blocks
    • For aziridinecarboxylate, see:, Yudin, A. K, Ed, Wiley-VCH: New York, Chapter 3
    • (b) For aziridinecarboxylate, see: Zhou, P.; Chen, B.-C.; Davis, F. A. Asymmetric syntheses with aziridinecarboxylate and aziridinephosphonate building blocks. In Aziridines and Epoxides in Organic-Synthesis; Yudin, A. K., Ed.; Wiley-VCH: New York, 2006; Chapter 3.
    • (2006) Aziridines and Epoxides in Organic-Synthesis
    • Zhou, P.1    Chen, B.-C.2    Davis, F.A.3
  • 13
    • 0038779270 scopus 로고    scopus 로고
    • For a useful overview of the synthesis of chiral oxirane-2-carboxylic acid derivatives, see:, and references therein
    • For a useful overview of the synthesis of chiral oxirane-2-carboxylic acid derivatives, see: Wang, M.-X.; Lin, S.-J.; Liu, C-S.; Zheng, Q.-Y.; Li, J.-S. J. Org. Chem. 2003, 68, 4570 and references therein.
    • (2003) J. Org. Chem , vol.68 , pp. 4570
    • Wang, M.-X.1    Lin, S.-J.2    Liu, C.-S.3    Zheng, Q.-Y.4    Li, J.-S.5
  • 29
    • 33845500079 scopus 로고    scopus 로고
    • Very recently, asymmetric aziridination of chalcones with an aminimide promoted by (+)-Tröger's base has been reported to give moderate enantiocontrol. Shen, Y.-M.; Zhao, M.-X.; Xu, J. Shi, Y. Angew. Chem.. Int. Ed. 2006, 45, 8005.
    • (f) Very recently, asymmetric aziridination of chalcones with an aminimide promoted by (+)-Tröger's base has been reported to give moderate enantiocontrol. Shen, Y.-M.; Zhao, M.-X.; Xu, J. Shi, Y. Angew. Chem.. Int. Ed. 2006, 45, 8005.
  • 75
    • 33947220579 scopus 로고
    • For pyramidal inversion of the aziridine ring, see:, 4th ed, John Wiley & Sons, Inc, New York, and references therein
    • For pyramidal inversion of the aziridine ring, see: March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons, Inc.: New York, 1992; pp 98-99 and references therein.
    • (1992) Advanced Organic Chemistry , pp. 98-99
    • March, J.1
  • 76
    • 33645451288 scopus 로고    scopus 로고
    • Very recently, benzyl bromide has also been used to open the 2-alkanoyloxymethyl-1-arylmentylaziridine ring. (a) D'hooghe, M.; Van Speybroeck, V.; Waroquier, M.; De Kimpe, N. Chem. Commun. 2006, 1554.
    • Very recently, benzyl bromide has also been used to open the 2-alkanoyloxymethyl-1-arylmentylaziridine ring. (a) D'hooghe, M.; Van Speybroeck, V.; Waroquier, M.; De Kimpe, N. Chem. Commun. 2006, 1554.
  • 78
    • 33744725551 scopus 로고    scopus 로고
    • The aziridinium intermediate was very recently proposed and utilized in the synthesis of enantiopure β-amino and α,β-diamino esters from the reaction of N,N-dibenzyl-O-methylsulfonyl serine methyl ester with nucleophilic reagents. Couturier, C, Blanchet, J, Schlama, T, Zhu, J. Org. Lett. 2006, 8, 2183
    • The aziridinium intermediate was very recently proposed and utilized in the synthesis of enantiopure β-amino and α,β-diamino esters from the reaction of N,N-dibenzyl-O-methylsulfonyl serine methyl ester with nucleophilic reagents. Couturier, C.; Blanchet, J.; Schlama, T.; Zhu, J. Org. Lett. 2006, 8, 2183.


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