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Volumn , Issue 8, 1999, Pages 1313-1315

Stereoselective conjugate addition of alkyl groups to (S)-4-(tert- butyldimethylsilyloxy)-2-phenylsulfonyl-2-cyclopentenone by means of trialkylaluminum reagents

Author keywords

Aluminum; Conjugate addition reaction; Cyclopentanone; Stereoselectivity; Sulfone

Indexed keywords

4 (TERT BUTYLDIMETHYLSILYLOXY) 3 ALKYL 2 PHENYLSULFONYLCYCLOPENTANONE; ALUMINUM; CYCLOPENTANONE DERIVATIVE; REAGENT; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032811141     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2823     Document Type: Article
Times cited : (8)

References (29)
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    • note
    • 4SSi: C, 58.66; H, 7.66. Found: C, 58.87; H, 7.51.
  • 21
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    • note
    • 2 produced 5. 8a (figure presented)
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    • 1H NMR data of H-2 and H-4 protons of 2a-d, 3, and 4
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    • note
    • The ratio of 3, 2d and 2b was estimated to be 51:31:18 by an integrated intensity of the peak heights of the signals due to the protons of the tert-butyl group appeared at δ 0.90, 0.84 and 0.81, respectively.
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    • For the chelation of metals with TBDMSoxy ketones, see: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778. For other examples, see: Bloch, R. Chem. Rev. 1998, 98, 1407.
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    • For the chelation of metals with TBDMSoxy ketones, see: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778. For other examples, see: Bloch, R. Chem. Rev. 1998, 98, 1407.
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    • note
    • An intriguing alternative to this mechanism would involve the formation of the chelated intermediate D. Unfortunately, the cis-selectivity of the ester 1b cannot be explained through a similar intermediate E.


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