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Volumn 70, Issue 26, 2005, Pages 10823-10840

Lewis base catalyzed aldol additions of chiral trichlorosilyl enolates and silyl enol ethers

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; CATALYSIS; CATALYSTS; KETONES; SILICON COMPOUNDS; STEREOCHEMISTRY;

EID: 30044441092     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051930+     Document Type: Article
Times cited : (42)

References (80)
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    • (b) Heathcock, C. H. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier; New York, 1984; Vol. 5B, pp 177-237.
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    • Carreira, E. M. In Comprehensive Asymmetric Catalysis, Vols. I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999. Chapter 29.
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  • 12
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    • Mahrwald, R., Ed.; Wiley-VCH: Weinheim
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    • (2001) Lewis Acids in Organic Synthesis , vol.1-2
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  • 31
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    • The configurational assignment of the major diastereomer as syn-28a was confirmed by single-crystal X-ray analysis of the diol 31 obtained by deprotection of TBS ether with PPTS in ethanol. (a) Martin, V. A.; Murray, D. H.; Pratt, N. E.; Zhao, Y.; Albizati, K. F. J. Am. Chem. Soc. 1990, 112, 6965-6968. Recrystallization of the crude diol provided a crystal suitable for X-ray analysis.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6965-6968
    • Martin, V.A.1    Murray, D.H.2    Pratt, N.E.3    Zhao, Y.4    Albizati, K.F.5
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    • (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
    • (b) The crystallographic coordinates of 31 have been deposited with the Cambridge Crystallographic Data Centre, deposition no. CCDC 270359. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 58
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    • The absolute configuration of the aldol products was assigned by analogy to the benzaldehyde aldol product. However, to ensure the consistency of stereoinduction from the catalyst system across the various aldehyde structures, the configuration of the β-hydroxy ketone obtained from pivaldehyde (syn-28k) was assigned by chemical correlation to the known acid 34 The site-selective Baeyer-Villiger oxidation of the ketone was accomplished using conditions developed by Shibasaki et al. to provide the ester 33 (Gottlich, R.; Yamakoshi, K.; Sasai, H.; Shibasaki, M. Synlett 1997, 971-973).
    • (1997) Synlett , pp. 971-973
    • Gottlich, R.1    Yamakoshi, K.2    Sasai, H.3    Shibasaki, M.4
  • 59
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    • The ester was hydrolyzed to the corresponding acid in good yield, the optical rotation of which compared well to the literature value of S-34. (Devant, R.; Braun, M. Chem. Ber. 1986, 119, 2191-2207). Thus, the sense of stereoinduction with (R,R)-1 was consistent between aldol additions to benzaldehyde and to pivaldehyde.
    • (1986) Chem. Ber. , vol.119 , pp. 2191-2207
    • Devant, R.1    Braun, M.2
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    • note
    • The configuration of the aldol product was confirmed by single-crystal X-ray analysis of the corresponding diol anti-38. The TBS group was removed from anti-35a under acidic conditions to give diol anti-38, which provided a crystal suitable for X-ray analysis from refluxing acetone/hexanes. The crystallographic coordinates of anti-38 have been deposited with the Cambridge Crystallographic Data Centre, deposition no. CCDC 270165. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
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    • note
    • The diastereoselectivities were assigned on the basis of chemical correlation to the known methyl ester.
  • 68
    • 0000560264 scopus 로고
    • The absolute configuration of the aldol product syn,anti-48a was determined by chemical correlation. First, the aldol product was converted to the corresponding ester 49 by Baeyer-Villiger oxidation with buffered m-CPBA (Bernhard, W.; Fleming, I. J. Organomet. Chem. 1984, 271, 281-288).
    • (1984) J. Organomet. Chem. , vol.271 , pp. 281-288
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    • Next, 49 was hydrolyzed under basic conditions to provide diol 50 in good yield. The configuration was assigned as (1S,2R)-1-phenylpropane-1,2-diol by comparing the sign of the optical rotation to the literature value, (a) Kihumbum, D.; Stillger, T.; Hummel, W.; Liese, A. Tetrahedron: Asymmetry 2002, 13, 1069-1072.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 1069-1072
    • Kihumbum, D.1    Stillger, T.2    Hummel, W.3    Liese, A.4
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    • note
    • The assignments for the relative anti diastereomers were made by analogy to the assignment of aldol products from ref 7c.
  • 74
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    • For a discussion of the coordinating abilities of various ether substituents, see: (a) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468.
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  • 77
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    • For a discussion of chelation as a stereocontrol element in lactate derived stannous enolate, see: Paterson, I.; Tillyer, R. D. Tetrahedron Lett. 1992, 33, 4233-4236.
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    • Ph.D. Thesis, University of Illinois at Urbana-Champaign, Urbana, Illinois
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.