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Volumn 129, Issue 9, 2007, Pages 2410-2411

Catalytic asymmetric rearrangement of α,α-disubstituted α-siloxy aldehydes to optically active acyloins using axially chiral organoaluminum Lewis acids

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALUMINUM DERIVATIVE; KETONE; LEWIS ACID; ORGANOMETALLIC COMPOUND;

EID: 33847609216     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063051q     Document Type: Article
Times cited : (58)

References (34)
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    • Pinacol-type rearrangement: (a) Suzuki, K.; Katayama, E.; Tsuchihashi, G. Tetrahedron Lett. 1983, 24, 4997.
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    • Epoxy ether rearrangement: (c) Maruoka, K.; Hasegawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 3827.
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    • For asymmetric synthesis of α-hydroxy ketones, see oxidation by chiral phase-transfer catalysis: a
    • For asymmetric synthesis of α-hydroxy ketones, see oxidation by chiral phase-transfer catalysis: (a) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835.
    • (1988) Tetrahedron Lett , vol.29 , pp. 2835
    • Masui, M.1    Ando, A.2    Shioiri, T.3
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    • Oxidation with chiral oxaziridines: (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679.
    • Oxidation with chiral oxaziridines: (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679.
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    • Dihydroxylation of enol ethers: (c) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067.
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    • Benzoin condensation: (d) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
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    • Nitroso aldol synthesis: (e) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038.
    • Nitroso aldol synthesis: (e) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038.
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    • For the results, see the Supporting Information
    • For the results, see the Supporting Information.
  • 23
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    • For detail, see the Supporting Information
    • For detail, see the Supporting Information.
  • 24
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    • 4 was obtained as two separable diastereomers in a (S,S)/(S,R) ratio of 8:1.
    • 4 was obtained as two separable diastereomers in a (S,S)/(S,R) ratio of 8:1.
  • 25
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    • 3-Al and 2-hydroxy-2′-(trifluoromethanesulfonylamino) biphenyl, see: Ooi, T.; Ichikawa, H.; Maruoka, K. Angew. Chem., Int. Ed. 2001, 40, 3610. The mode of aggregation of 3 in solution is unclear at present.
    • 3-Al and 2-hydroxy-2′-(trifluoromethanesulfonylamino) biphenyl, see: Ooi, T.; Ichikawa, H.; Maruoka, K. Angew. Chem., Int. Ed. 2001, 40, 3610. The mode of aggregation of 3 in solution is unclear at present.
  • 26
    • 33847622830 scopus 로고    scopus 로고
    • Unfortunately, the present system is not effective for symmetrically α,α-diaryl-substituted α-siloxy aldehydes
    • Unfortunately, the present system is not effective for symmetrically α,α-diaryl-substituted α-siloxy aldehydes.
  • 27
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    • For a recent review on nonenzymatic kinetic resolution, see
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    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 3974
    • Vedejs, E.1    Jure, M.2
  • 28
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    • Tertiary α-hydroxy aldehydes are versatile chiral building blocks in natural product syntheses. See, for example: (a) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron 2002, 58, 5909.
    • Tertiary α-hydroxy aldehydes are versatile chiral building blocks in natural product syntheses. See, for example: (a) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron 2002, 58, 5909.
  • 30
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    • The s values in this communication were calculated based on conversion and ee of 5 assuming first-order dependence on 5. For discussion on the validity of calculated s values, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
    • The s values in this communication were calculated based on conversion and ee of 5 assuming first-order dependence on 5. For discussion on the validity of calculated s values, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
  • 33
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    • Attempted treatment of 5a with (S,S)-3 (10 mol %) in toluene at -20 °C for 48 h furnished 6a quantitatiuvely with 8% ee (S).
    • Attempted treatment of 5a with (S,S)-3 (10 mol %) in toluene at -20 °C for 48 h furnished 6a quantitatiuvely with 8% ee (S).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.