메뉴 건너뛰기




Volumn , Issue 8, 2006, Pages 1981-1990

Unexpected selectivity in sodium borohydride reductions of α-substituted esters: Experimental and theoretical studies

Author keywords

Borohydrides; Chemoselectivity; Density functional calculations; Esters; Reduction

Indexed keywords


EID: 33646189527     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500824     Document Type: Article
Times cited : (21)

References (46)
  • 15
    • 0037178543 scopus 로고    scopus 로고
    • For some recent experimental studies on the reductions of ketonesters with sodium borohydride, see: a) P. V. Ramachandran, S. Pitre, H. C. Brown, J. Org. Chem. 2002, 67, 5315;
    • (2002) J. Org. Chem. , vol.67 , pp. 5315
    • Ramachandran, P.V.1    Pitre, S.2    Brown, H.C.3
  • 18
    • 0041837304 scopus 로고    scopus 로고
    • 4 selective reductions of α,β-unsaturated diene reductions, see: a) B. C. Ranu, S. Samanta, J. Org. Chem. 2003, 68, 7130;
    • (2003) J. Org. Chem. , vol.68 , pp. 7130
    • Ranu, B.C.1    Samanta, S.2
  • 27
    • 0025696553 scopus 로고
    • For selective reductions of aldehyde groups with ketone functions in the same molecule to form keto alcohols, see: c) B. C. Ranu, R. Chakraborty, Tetrahedron Lett. 1990, 31, 7663-7664.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7663-7664
    • Ranu, B.C.1    Chakraborty, R.2
  • 36
    • 33646165209 scopus 로고    scopus 로고
    • note
    • -1 in THF. Since Ph is bigger than Me, the barrier of reduction of N-methylbenzamide would be larger than that for N-methylacetamide.
  • 38
    • 33646169738 scopus 로고    scopus 로고
    • note
    • 4/ester complex. Subsequent aldehyde formation and reduction to alcohol in several steps exhibited lower barriers. Thus, our calculations reported here focus on hydride attack on the ester carbonyl carbon.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.