메뉴 건너뛰기




Volumn , Issue 12, 1999, Pages 3421-3427

One-pot and sequential asymmetric hydrogenation of β,δ-diketoesters into functionalized 1,3-diols: From anti- to syn-stereoselectivity

Author keywords

3,5 Dioxoester; Asymmetric hydrogenation; Diols; Lactone; Ruthenium catalyst

Indexed keywords

DIKETONE; HEXANOIC ACID DERIVATIVE; RUTHENIUM;

EID: 0032758041     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3421::AID-EJOC3421>3.0.CO;2-1     Document Type: Article
Times cited : (38)

References (37)
  • 2
    • 0344142920 scopus 로고    scopus 로고
    • For an easier reading of this manuscript, we used the same system for numbering compounds as adopted by Saburi et al.[1]
    • For an easier reading of this manuscript, we used the same system for numbering compounds as adopted by Saburi et al.[1]
  • 14
    • 0344142957 scopus 로고    scopus 로고
    • note
    • 3 as catalyst precursor (Table 1, entry 1), and (ii) scalemic samples of 2 prepared with catalysts bearing ligands of opposite configuration; see note[18].
  • 17
    • 0345436549 scopus 로고    scopus 로고
    • note
    • 2Me. β-Diketones show comparable enolization equilibrium data, and it is therefore likely that 1 interacts with the Ru species in a similar way as β-diketones do. [1]
  • 26
    • 0345436546 scopus 로고    scopus 로고
    • note
    • 3 can be assumed.
  • 27
    • 0344574361 scopus 로고    scopus 로고
    • note
    • Experiments conducted with the (S)-A/TFA catalytic system in other solvents showed that methyl acetate induces the formation of a ca. 50/50 mixture of syn-3 and anti-3, while the reaction proceeds very slowly in toluene and chloroform and is not chemoselective at all in pure methanol.
  • 30
    • 0344574360 scopus 로고    scopus 로고
    • note
    • 2[(S)-MeO-Biphep] and (S)-11, and led to (S,S)-9 in almost identical diastereo- and enantioselectivities.
  • 31
    • 0344574358 scopus 로고    scopus 로고
    • note
    • 2 gave after 47 h a 55/45 mixture of syn-2/lanti-2 (100% conversion, 99%, combined selectivity into 2 and 3), with 4% ee (3R,5R) and 54% ee (3S,5R), respectively; lactone 5 was then recovered in 25% ee (R).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.