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Volumn 38, Issue 3, 2009, Pages 296-297

Catalytic use of Strontium hexamethyldisilazide in the asymmetric Michael addition of malonate to chalcone derivatives

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EID: 67650492786     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.296     Document Type: Article
Times cited : (20)

References (43)
  • 1
    • 34250613134 scopus 로고    scopus 로고
    • For recent reviews on Michael additions, see: a
    • For recent reviews on Michael additions, see: a) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701.
    • (2007) Eur. J. Org. Chem , pp. 1701
    • Tsogoeva, S.B.1
  • 29
    • 67650484935 scopus 로고    scopus 로고
    • For a recent example of catalyst-free Michael additions, see
    • For a recent example of catalyst-free Michael additions, see: T. Kakinuma, R. Chiba, T. Oriyama, Chem. Lett. 2008, 37, 1204.
    • (2008) Chem. Lett , vol.37 , pp. 1204
    • Kakinuma, T.1    Chiba, R.2    Oriyama, T.3
  • 32
    • 67650351699 scopus 로고    scopus 로고
    • For sporadic examples of strontium catalysis, see
    • For sporadic examples of strontium catalysis, see:
  • 39
    • 0002377491 scopus 로고
    • this strontium amide compound appears to have a dimeric structure. For the preparation of strontium hexamethyldisilazide, see
    • For the preparation of strontium hexamethyldisilazide, see: M. Westerhausen, Inorg. Chem. 1991, 30, 96, this strontium amide compound appears to have a dimeric structure.
    • (1991) Inorg. Chem , vol.30 , pp. 96
    • Westerhausen, M.1
  • 40
    • 14644424554 scopus 로고    scopus 로고
    • For the preparation of these types of bis (sulfonamide) ligands, see: a
    • For the preparation of these types of bis (sulfonamide) ligands, see: a) R. Hilgraf, A. Pfaltz, Adv. Synth. Catal. 2005, 347, 61.
    • (2005) Adv. Synth. Catal , vol.347 , pp. 61
    • Hilgraf, R.1    Pfaltz, A.2
  • 43
    • 84869345013 scopus 로고    scopus 로고
    • Typical experimental procedure for the Sr-catalyzed Michael addition: In a flame-dried 30-mL flask, a suspension of Sr (HMDS) 2 (6.1 mg, 0.015 mmol, 5 mol , chiral ligand L* (9.9 mg, 0.018 mmol, 6 mol , and MS 4A (100 mg) in dry toluene (1.0 mL) was stirred for 2h at room temperature under an argon atmosphere. After this period, solutions of di-n-propyl malonate (1; 67.1 μL, 0.36 mmol, 1.2 equiv) in toluene (1.0 mL) and the corresponding chalcone 2 or 4 (0.30 mmol) in toluene (1.0 mL) were successively added. After the indicated reaction time, the crude mixture was quenched with sat. aq NH4Cl (10 mL, After addition of CH 2Cl2, the organic layer was separated and the aqueous layer was extracted with CH2Cl2 three times, The combined organic layers were then dried over anhydrous Na2SC 4, filtered and concentrated under reduced pressure. The corresponding crud
    • 4, filtered and concentrated under reduced pressure. The corresponding crude product was purified by preparative thin-layer chromatography (PTLC; hexane-ethyl acetate) to afford the desired product 3 or 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.