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Volumn , Issue 24, 2009, Pages 4073-4084

N-allylideneamines derived from acrolein: synthesis and use as acceptors of two nucleophiles

Author keywords

Allylic compounds; Amines; Amino acids; Nucleophilic addition; Regioselectivity

Indexed keywords


EID: 68349090113     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900457     Document Type: Article
Times cited : (15)

References (46)
  • 15
    • 68349083872 scopus 로고    scopus 로고
    • Although we examined the 1,4- and 1,2-double nucleophilic addition using the imine protected with the TBS group, the 1,4-1,2 product was not obtained
    • Although we examined the 1,4- and 1,2-double nucleophilic addition using the imine protected with the TBS group, the 1,4-1,2 product was not obtained.
  • 16
    • 68349119597 scopus 로고    scopus 로고
    • When the 1,4- and 1,2-double nucleophilic addition with the α,β-unsaturated imine bearing an electron-withdrawing group was investigated, the 1,4-addition product was obtained instead of the 1,4-1,2 adduct
    • When the 1,4- and 1,2-double nucleophilic addition with the α,β-unsaturated imine bearing an electron-withdrawing group was investigated, the 1,4-addition product was obtained instead of the 1,4-1,2 adduct.
  • 30
    • 68349106186 scopus 로고    scopus 로고
    • Calculations were carried out by using the SPARTAN pro program. 6-3IG* calculations were also carried out by using MOPAC PC SPARTAN pro, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvin, CA 926.12, USA, 1999.
    • Calculations were carried out by using the SPARTAN pro program. 6-3IG* calculations were also carried out by using MOPAC PC SPARTAN pro, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvin, CA 926.12, USA, 1999.
  • 31
    • 68349119598 scopus 로고    scopus 로고
    • Results for the s-cis isomers are nearly the same as those for the s-trans; the difference in the method of calculation (HF/ STO-3G or PM3) has little influence on a qualitative conclusion.
    • Results for the s-cis isomers are nearly the same as those for the s-trans; the difference in the method of calculation (HF/ STO-3G or PM3) has little influence on a qualitative conclusion.
  • 32
    • 33746310614 scopus 로고    scopus 로고
    • For examples using silica gel. as a reaction promoter, see
    • For examples using silica gel. as a reaction promoter, see: M. Shimizu, M. Tanaka, T. Itho, I. Hachiya, Synlett 2006, 1687-1690.
    • (2006) Synlett , pp. 1687-1690
    • Shimizu, M.1    Tanaka, M.2    Itho, T.3    Hachiya, I.4
  • 33
    • 68349103590 scopus 로고    scopus 로고
    • 1H NMR spectroscopy that 1,4- and 1,2addition products 7ac, 7ad, and 7af were converted into 1,4 adducts by a retro-Strecker reaction (Table 7, Entries 3, 4, and 6). Because the adducts were not stable, the addition reactions with lb were not examined in detail.
    • 1H NMR spectroscopy that 1,4- and 1,2addition products 7ac, 7ad, and 7af were converted into 1,4 adducts by a retro-Strecker reaction (Table 7, Entries 3, 4, and 6). Because the adducts were not stable, the addition reactions with lb were not examined in detail.
  • 44
    • 33748661764 scopus 로고    scopus 로고
    • The regioselectivity of the addition of nucleophiles to α,β-unsaturated aldimines has been studied previously, see ref. For examples using α,β-unsaturated aldimines for the β-lactam synthesis, see: a
    • The regioselectivity of the addition of nucleophiles to α,β-unsaturated aldimines has been studied previously, see ref. For examples using α,β-unsaturated aldimines for the β-lactam synthesis, see: a) I. Fleming, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 1998, 2663-2671;
    • (1998) J. Chem. Soc. Perkin Trans. 1 , pp. 2663-2671
    • Fleming, I.1    Kilburn, J.D.2
  • 46
    • 68349108904 scopus 로고    scopus 로고
    • A control experiment was carried out by using acrolein as the substrate in place of the imine 1c. Under the conditions A in Table 8, the reaction gave the 1,4- and 1,2-addition product in 36% yield.
    • A control experiment was carried out by using acrolein as the substrate in place of the imine 1c. Under the conditions A in Table 8, the reaction gave the 1,4- and 1,2-addition product in 36% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.