메뉴 건너뛰기




Volumn 126, Issue 13, 2004, Pages 4245-4255

Catalytic, Asymmetric α-Chlorination of Acid Halides

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINATION; ESTERIFICATION; HALOGENATION; REACTION KINETICS;

EID: 1842555125     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039046t     Document Type: Article
Times cited : (107)

References (61)
  • 18
    • 0033920416 scopus 로고    scopus 로고
    • It is useful to distinguish between asymmetric processes in which halogen adds as either an electrophile or a nucleophile. The latter category includes the enantioselective opening of meso epoxides: Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 421-431
    • Jacobsen, E.N.1
  • 20
    • 0003828015 scopus 로고
    • John Wiley & Sons: New York
    • (a) Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995.
    • (1995) Ketenes
    • Tidwell, T.T.1
  • 23
    • 0001119728 scopus 로고
    • Chiral ammonium enolates have been shown to be the reactive intermediates in a number of asymmetric transformations. For examples, see: (a) Wynberg, H.; Staring, E. G. J. Am. Chem. Soc. 1982, 104, 166-168.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 166-168
    • Wynberg, H.1    Staring, E.G.2
  • 27
    • 0041878745 scopus 로고    scopus 로고
    • For other timely uses of cinchona alkaloids in catalytic asymmetric synthesis and others contained therein: France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985-3012.
    • (2003) Chem. Rev. , vol.103 , pp. 2985-3012
    • France, S.1    Guerin, D.J.2    Miller, S.J.3    Lectka, T.4
  • 28
    • 0034676531 scopus 로고    scopus 로고
    • Cinchona alkaloid derivatives have recently been used as stoichiometric reagents for asymmetric halogenation: (a) Cahard, D.; Audouard, C.; Plaquevent, J.-C.; Roques, N. Org. Lett. 2000, 2, 3699-3701.
    • (2000) Org. Lett. , vol.2 , pp. 3699-3701
    • Cahard, D.1    Audouard, C.2    Plaquevent, J.-C.3    Roques, N.4
  • 39
    • 1842618418 scopus 로고    scopus 로고
    • note
    • Proofs of absolute configuration were determined on the basis of conversion to the known methyl ester and a known α-thio derivative. Stereoregularity was inferred for other products on the basis of these proofs as well as on the basis of computational models. See Supporting Information.
  • 45
    • 1842461715 scopus 로고    scopus 로고
    • note
    • + shows a strong preference for a bent geometry.
  • 46
    • 1842566287 scopus 로고    scopus 로고
    • note
    • We used the program Macromodel (version 7.0) for the calculations (Schrodinger, Inc.).
  • 48
    • 0034697472 scopus 로고    scopus 로고
    • Short C-H-O distances have been identified in organic compounds and also in nucleic acid molecules. These interactions have been studied in detail, with an emphasis on the application of crystal correlation studies. Due to their influence in crystal packing, studies are underway to ascertain the extent to which these interactions affect C-H approach to an oxygen atom. For mechanistic and theorical discussions of C-H-O interactions, see: (a) Calhorda, M. J. Chem. Commun. 2000, 801-809.
    • (2000) Chem. Commun. , pp. 801-809
    • Calhorda, M.J.1
  • 53
    • 1842461719 scopus 로고    scopus 로고
    • note
    • Kinetics experiments were performed by varying the concentration of chlorinating agent 5a, BQ catalyst, and acid chloride substrate, and measuring the percent conversion at various times (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.