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Tetrahedron Letters
Volumn 36, Issue 31, 1995, Pages 5461-5464
A new general method for preparation of N-methoxy-N-methylamides. Application in direct conversion of an ester to a ketone
Author keywords

[No Author keywords available]
Indexed keywords

17BETA BENZOYL 4 AZA 5ALPHA ANDROST 1 EN 3 ONE; AMIDE; AZASTEROID; MK 434; STEROID 5ALPHA REDUCTASE INHIBITOR; UNCLASSIFIED DRUG;
EID: 0029084414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)01089-Z     Document Type: Article
Times cited : (278)
References (21)
  • 5
    • 84914006839 scopus 로고    scopus 로고
    • Bhattacharya, A.; Douglas, A. W.; Grabowski, E. J. J.; Dolling, U.-H. U.S. Patent 5,084,574, 1992.
  • 7
    • 84914006838 scopus 로고    scopus 로고
    • Williams, J. M.; Dolling, U.-H. U.S. Patent 5,061,801, 1991.
  • 11
    • 0000155765 scopus 로고
    • The nucleophilicity of an anion bearing an α-heteroatom is enhanced, the α effect, and references cited therein. The rate enhancement observed for the addition of hydroperoxide to an ester carbonyl in comparison to hydroxide is exemplary
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2349
    • Evanseck1    Blake2    Jorgensen3
  • 13
    • 0001666417 scopus 로고
    • It has been suggested that the reagent formed from Me(MeO)NH and MeLi undergoes self-decomposition
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6016
    • Beak1    Basha2    Kokko3    Loo4
  • 14
    • 84914006837 scopus 로고    scopus 로고
    • The reaction of an organolithium reagent with Me(MeO)NH/MeLi results in efficient displacement of methoxide at the amide nitrogen to give the lithium amide of a secondary amine. The reaction with an organomagnesium reagent is less efficient. Beak, P.; Selling, G. W. J. Org. Chem. 1989, 54, 5574.
  • 15
    • 0001597804 scopus 로고
    • The enhanced nucleophilicity and low basicity of this amide reagent should allow use with a wide variety of carboxylic acid derivatives including α-chiral oxazolidinones without epimerization, It might also be possible to develop a method for transient protection of ketones
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6141
    • Evans1    Britton2    Ellman3
  • 16
    • 85022533095 scopus 로고
    • The Synthetic Utility of α-Amino Alkoxides
    • (1992) Synlett , pp. 615
    • Comins1
  • 17
    • 0025133334 scopus 로고
    • Amide bases promote conversion of N-methoxy-N-methylamides to N-hydroxymethyl-N-methylamides and N-methylamides, The reaction parameters have not been optimized and, presumably, this problem could be minimized by adjusting the amine hydrochloride/i-PrMgCl charges.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6269
    • Graham1    Scholz2
  • 21
    • 84914006836 scopus 로고    scopus 로고
    • Estimated yields for five ester/organomagnesium pairs ranged from 46 to 77% with unreacted N-methoxy-N-methylamide ranging from 7 to 16%.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.