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Volumn 54, Issue 37, 1998, Pages 11255-11270

Lithiated (E)-N-isopropyl-5-tosyl-4-pentenamide: Synthetic applications as new δ-acyldienyl anion equivalent

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; ALKENE DERIVATIVE; AMIDE; ANION; CARBOXYLIC ACID DERIVATIVE; HALIDE; ISOCYANIC ACID DERIVATIVE; LACTAM; LITHIUM; PROPYLENE OXIDE; SULFONE;

EID: 0032505224     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00658-9     Document Type: Article
Times cited : (9)

References (31)
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    • 1. For recent reviews about polyene macrolide antibiotics see: (a) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
    • (1995) Chem. Rev. , vol.95 , pp. 2021-2040
    • Rychnovsky, S.D.1
  • 3
    • 0004298799 scopus 로고    scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier Science, in the press
    • 2. For a recent review about natural products with polyene amide structures see: Nájera, C.; Yus, M. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science, Vol. 21 in the press.
    • Studies in Natural Products Chemistry , vol.21
    • Nájera, C.1    Yus, M.2
  • 4
    • 0000606066 scopus 로고
    • These dianions are alkylated at the allylic position, the resulting thioesters after LDA-promoted [2.3]-sigmatropic rearrangement to the 2-mercaptocarboxylic esters and S-methylation and oxidation to the sulfoxides followed by thermal dehydrosulfenylation afforded (2E,4E)-dienoates
    • 3. These dianions are alkylated at the allylic position, the resulting thioesters after LDA-promoted [2.3]-sigmatropic rearrangement to the 2-mercaptocarboxylic esters and S-methylation and oxidation to the sulfoxides followed by thermal dehydrosulfenylation afforded (2E,4E)-dienoates: Tanaka, K.; Terauchi, M.; Kaji, A. Chem. Lett. 1981, 315-318.
    • (1981) Chem. Lett. , pp. 315-318
    • Tanaka, K.1    Terauchi, M.2    Kaji, A.3
  • 7
    • 85038530762 scopus 로고    scopus 로고
    • private communication
    • 5. Bernabeu, M. C. private communication.
    • Bernabeu, M.C.1
  • 9
    • 0342275178 scopus 로고    scopus 로고
    • and references cited therein
    • 7. For recent studies about lithiated vinyl sulfones see: Caturla, F.; Nájera, C. Tetrahedron 1997, 53, 11449-11464 and references cited therein.
    • (1997) Tetrahedron , vol.53 , pp. 11449-11464
    • Caturla, F.1    Nájera, C.2
  • 11
    • 37049087545 scopus 로고
    • 9. This is an appropriate methodology for the stereoselective introduction of the arylsulfonyl group at the terminal position of olefins: (a) Nájera, C.; Baldó, B.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1988, 1029-1032.
    • (1988) J. Chem. Soc., Perkin Trans. 1 , pp. 1029-1032
    • Nájera, C.1    Baldó, B.2    Yus, M.3
  • 15
    • 85038532741 scopus 로고    scopus 로고
    • 1H NMR (300 MHz)
    • 1H NMR (300 MHz)
  • 16
    • 85038537875 scopus 로고    scopus 로고
    • The deuterium incorporation was determined by mass spectrometry
    • 12. The deuterium incorporation was determined by mass spectrometry.
  • 17
    • 84990149267 scopus 로고
    • 13. The obtention of dideuterated lactam 26 is not a proof of the existence of dilithiated lactam 25. We have proposed the possible participation of this intermediate on the basis that monolithiated lactam 23 did not react with carbonyl compounds to give compounds 15. With respect to the structure, in the solid state the lithium is on the oxygen in lithiosulfones according to the X-ray analysis: (a) Hollstein, W.; Harms, K.; Marsch, M.; Boche, G. Angew. Chem. Int. Ed. Engl. 1988, 27, 846-849.
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 846-849
    • Hollstein, W.1    Harms, K.2    Marsch, M.3    Boche, G.4
  • 19
    • 0000084040 scopus 로고
    • 14. For reviews about β-amido and β-oxido organolithium compounds see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
    • (1991) Trends Org. Chem. , vol.2 , pp. 155-181
    • Nájera, C.1    Yus, M.2
  • 21
    • 85038534530 scopus 로고    scopus 로고
    • threo = 2.5 Hz. (equation presented)
    • threo = 2.5 Hz. (equation presented)
  • 22
    • 0030978514 scopus 로고    scopus 로고
    • 16. Lithiated β-aminoalkyl sulfones gave also stereoselective dimerization to the meso diastereomers: Alonso, D. A.; Costa, A.; Mancheño, B.; Nájera, C. Tetrahedron 1997, 53, 4791-4814.
    • (1997) Tetrahedron , vol.53 , pp. 4791-4814
    • Alonso, D.A.1    Costa, A.2    Mancheño, B.3    Nájera, C.4
  • 23
    • 85038533247 scopus 로고    scopus 로고
    • threo = 2.0 Hz
    • threo = 2.0 Hz.
  • 25
    • 0027751768 scopus 로고
    • 19. Related 6-hydroxydienoates have been used as precursors of the polyhydroxy indolizidine alkaloid castanospermine by means of successive Sharpless epoxidation-dihydroxylation reactions of the two double carbon-carbon bonds: Kim, N. S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099.
    • (1993) J. Org. Chem. , vol.58 , pp. 7096-7099
    • Kim, N.S.1    Choi, J.-R.2    Cha, J.K.3
  • 29
    • 85038535992 scopus 로고    scopus 로고
    • Only one diastereomer
    • 23. Only one diastereomer.
  • 30
    • 85038533049 scopus 로고    scopus 로고
    • Mixture of diastereomers
    • 24. Mixture of diastereomers.
  • 31
    • 85038536192 scopus 로고    scopus 로고
    • + signal
    • + signal.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.