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Volumn 61, Issue 20, 1996, Pages 6758-6759

Diastereoselective uncatalyzed conjugate addition of organoaluminum reagents: Efficient desymmetrization of (R)-[(p-Tolylsulfinyl)methyl]quinols

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EID: 0001608015     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961126a     Document Type: Article
Times cited : (32)

References (34)
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    • note
    • 3 of the ethyl substituent (δ = 0.78 ppm) as a consequence of the anisotropic effect exerted by the spatially close aromatic ring. A similar effect could be observed in the proton or methyl group situated on the pro-R double bond of p-quinols 1 and 2.
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    • For recent references see: (a) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995, 317. (b) Kabbara, J.; Flemming, S.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron 1995, 51, 743. (b) Westermann, J.; Nickisch, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1368.
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    • For recent references see: (a) Flemming, S.; Kabbara, J.; Nickisch, K.; Neh, H.; Westermann, J. Synthesis 1995, 317. (b) Kabbara, J.; Flemming, S.; Nickisch, K.; Neh, H.; Westermann, J. Tetrahedron 1995, 51, 743. (b) Westermann, J.; Nickisch, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1368.
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    • note
    • 3. In this way, a 45:55 mixture of 4a and 4b was obtained. Thus, the result of the experience mentioned in the text suggests the mechanism proposed.


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