Asymmetric Michael addition of silyl nitronates to cyclic α,β-unsaturated ketones catalyzed by chiral quaternary ammonium bifluorides: Isolation and selective functionalization of enol silyl ethers of optically active γ-nitro ketones

Tetrahedron Letters

Volumn 47, Issue 2, 2006, Pages 145-148

  Ooi, Takashi ^a   Doda, Kanae ^a   Takada, Saki ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Nitro ketones; Chiral quaternary ammonium bifluorides; Cyclic enones; Enol silyl ethers; Michael addition; Silyl nitronates

Indexed keywords

ALCOHOL DERIVATIVE; ETHER DERIVATIVE; FLUORIDE; KETONE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHIRALITY; DERIVATIZATION; ENANTIOSELECTIVITY; GAS LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 28644434112     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.154     Document Type: Article

References (20)

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2. For an account of our contributions to this area, see: T. Ooi, and K. Maruoka Acc. Chem. Res. 37 2004 526
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8. For a recent excellent review on conjugate addition of nitroalkanes to electron deficient olefins, see: R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, and M. Petrini Chem. Rev. 105 2005 933
9. For reviews on catalytic asymmetric conjugate addition of stabilized carbanions, see: M. Yamaguchi E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 3, Chapter 31.2 1999 Springer Berlin
10. M. Yamaguchi E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Supplement 1 2004 Springer Berlin 151
11. For our recent contribution, see: T. Ooi, S. Takada, S. Fujioka, and K. Maruoka Org. Lett. 7 2005 5143
12. T. Ooi, K. Doda, and K. Maruoka J. Am. Chem. Soc. 125 2003 2054
13. For the use of this type of ammonium bromide as chiral phase-transfer catalyst, see: T. Ooi, M. Taniguchi, M. Kameda, and K. Maruoka Angew. Chem., Int. Ed. 41 2002 4542
14. T. Ooi, M. Kameda, M. Taniguchi, and K. Maruoka J. Am. Chem. Soc. 126 2004 9685
15. T. Ooi, S. Fujioka, and K. Maruoka J. Am. Chem. Soc. 126 2004 11790
16. w = 0.1280..
17. 1H NMR analysis, which was also supported by the crystal structure of acetal 8. See Ref. 8.
18. T. Ooi, R. Goto, and K. Maruoka J. Am. Chem. Soc. 125 2003 10494
19. b of the α-phenylation product 6 was 13.0 Hz, indicating their 1,2-diaxial alignments..
20. The relative stereochemistry was not determined.