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33746188818
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note
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Although the resulting products are more appropriately labeled acyloins rather than benzoins, we have adopted the term benzoin reaction as a general rubric for the nucleophilic addition of aldehydes to carbonyl compounds by the transient intermediacy of an acyl anion equivalent. Although imperfect, this nomenclature avoids confusion with the acyloin reaction, a fundamentally different process that affords otherwise identical products.
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note
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This work was presented in full at the Pacifichem Conference 2005 in Honolulu, Hawaii, USA, December 20, 2005 and the 85th CSJ Spring Meeting in Kanagawa University, Japan, March 26, 2005.
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41
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0037459877
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For the preparation of the ketoaldehyde substrates, see: a) J. W. Bode, Y. Hachisu, T. Matsuura, K. Suzuki, Tetrahedron Lett. 2003, 44, 3555-3558;
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c) T. Matsuura, J. W. Bode, Y. Hachisu, K. Suzuki, Synlett 2003, 11, 1746-1748.
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46
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33746212480
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note
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The absolute configurations of the tertiary alcohols were confirmed by X-ray analysis of the derived (S)-camphanyl esters following studies to confirm the chiral integrity of benzoin products under the esterification conditions (see the Supporting Information for details).
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