메뉴 건너뛰기




Volumn 74, Issue 22, 2009, Pages 8893-8896

Synthesis and reactivity of β-methoxymethyl enecarbamates

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; ELECTRON-RICH AROMATICS; LEWIS ACID; METHOXY; METHOXYMETHYL; SILYL ENOL ETHERS; SINGLE-STEP;

EID: 70449623123     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901992z     Document Type: Article
Times cited : (10)

References (46)
  • 1
  • 27
    • 70449661931 scopus 로고    scopus 로고
    • note
    • The methylenated adducts 1, 2, and 13 were stable for at least a month when stored below 0°C. However, prolonged storage resulted in gradual decomposition.
  • 28
    • 70449692432 scopus 로고    scopus 로고
    • note
    • Gas phase density functional calculations performed at the B3LYP/6-31 +G(d)//B3LYP/6-31+G(d) level support the conclusion that 1 is thermodynamically favored over 6 with a Boltzmann distribution of 98:2 based on unscaled zeropoint corrected electronic energies at 298 K (ΔE=9.78 kJ/mol). See the Supporting Information for computational details.
  • 33
    • 0032887207 scopus 로고    scopus 로고
    • The homo- and heterodimerization of enecarbamates has been reported; see ref 3 and
    • The homo- and heterodimerization of enecarbamates has been reported; see ref 3 and: Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D. J. Org. Chem. 1999, 64, 6646-6652.
    • (1999) J. Org. Chem. , vol.64 , pp. 6646-6652
    • Oliveira, D.F.1    Miranda, P.C.M.L.2    Correia, C.R.D.3
  • 34
    • 33846986839 scopus 로고    scopus 로고
    • Conventional heating gave significant amounts of starting material 12 and N,O-acetal 9 byproduct. Microwave-assisted organocatalytic Mannich reactions have been described, see
    • Conventional heating gave significant amounts of starting material 12 and N,O-acetal 9 byproduct. Microwave-assisted organocatalytic Mannich reactions have been described, see: (a)Hosseini,M.; Stiasni, N.;Barbieri, V.; Kappe, C. O. J. Org. Chem. 2007, 72, 1417-1424.
    • (2007) J. Org. Chem. , vol.72 , pp. 1417-1424
    • Hosseini, M.1    Stiasni, N.2    Barbieri, V.3    Kappe, C.O.4
  • 39
    • 70449685109 scopus 로고    scopus 로고
    • note
    • The C1′ alkylated adduct of 1 with anisole (cf. adduct 22) is predicted be thermodynamically favored over the C2 adduct by 37.7 kJ/mol based on unscaled zero-point corrected electronic energies at 298 K. See the Experimental Section for computational details.
  • 40
    • 0028824251 scopus 로고
    • N-Acyliminium cyclizations are used extensively for the construction of heterocyclic ring systems; see
    • N-Acyliminium cyclizations are used extensively for the construction of heterocyclic ring systems; see: (a) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107-8110.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8107-8110
    • Marson, C.M.1    Pink, J.H.2    Smith, C.3
  • 45
    • 33749436403 scopus 로고    scopus 로고
    • The asymmetric hydrogenation of β-acyl enecarbamates has been demonstrated, see
    • The asymmetric hydrogenation of β-acyl enecarbamates has been demonstrated, see: Lei, A.; Chen, M.; He, M.; Zhang, X. Eur. J. Org. Chem. 2006, 19, 4343-4347.
    • (2006) Eur. J. Org. Chem. , vol.19 , pp. 4343-4347
    • Lei, A.1    Chen, M.2    He, M.3    Zhang, X.4
  • 46
    • 70449661929 scopus 로고    scopus 로고
    • note
    • Dynamic NMR effects due to hindered rotation about the CO-N bond.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.