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Volumn 52, Issue 22, 2011, Pages 2834-2836

Trichlorosilyl triflate for enantioselective direct-type aldol reaction with chiral phosphine oxide

Author keywords

Aldol reaction; Enantioselective catalysis; Lewis base; Phosphine oxide; Trichlorosilyl triflate

Indexed keywords

ALDEHYDE; KETONE; LEWIS BASE; NONOXINOL; PHOSPHINE OXIDE DERIVATIVE; TRICHLOROSILYL TRIFLATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 79955560732     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.095     Document Type: Article
Times cited : (32)

References (52)
  • 1
    • 33646555477 scopus 로고    scopus 로고
    • For reviews on Lewis base organocatalysts, see: Y. Orito, and M. Nakajima Synthesis 2006 1391
    • (2006) Synthesis , pp. 1391
    • Orito, Y.1    Nakajima, M.2
  • 16
    • 33646557046 scopus 로고    scopus 로고
    • For phosphine oxide-catalyzed enantioselective aldol reactions of trichlrosilyl enol ethers, S. Kotani, S. Hashimoto, and M. Nakajima Synlett 2006 1116
    • (2006) Synlett , pp. 1116
    • Kotani, S.1    Hashimoto, S.2    Nakajima, M.3
  • 18
    • 31944440611 scopus 로고    scopus 로고
    • For recent papers for other applications of Lewis base to asymmetric aldol reactions, see: S.E. Denmark, and J.R. Heemstra Jr. J. Am Chem. Soc. 128 2006 1038
    • (2006) J. Am Chem. Soc. , vol.128 , pp. 1038
    • Denmark, S.E.1    Heemstra Jr., J.R.2
  • 25
    • 79955555357 scopus 로고    scopus 로고
    • note
    • In the aldol reaction of trichlorosilyl enol ethers using BINAPO, more than 90% ee was observed at -78 °C, see: Ref. 4.
  • 49
    • 79955570943 scopus 로고    scopus 로고
    • note
    • The dichloromethane solution of trichlorosilyl triflate was storable in a refrigerator in a screw-top bottle. No loss of activity has been observed for a month.
  • 50
    • 79955559653 scopus 로고    scopus 로고
    • note
    • The yield of the aldol adduct at -78 °C was quite low and the diastereoselectivity was comparable to that at -40 °C.
  • 51
    • 79955553093 scopus 로고    scopus 로고
    • note
    • The reaction of 1b and 2a in the absence of BINAPO was completed within 5 min and the corresponding syn-isomer was produced predominantly (83% yield, syn:anti = 85:15).
  • 52
    • 79955567754 scopus 로고    scopus 로고
    • note
    • 1-Boc-4-piperidone was less reactive, yielding the product in low chemical yield and stereoselectivity (24% yield, syn:anti = 28:72, 33% ee (anti)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.