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Synfacts 2011(8): 0859-0859  
DOI: 10.1055/s-0030-1260832
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Umpolung Allylation of Aldehydes

Contributor(s): Mark Lautens, Jane Panteleev
S.-F. Zhu, X.-C. Qiao, Y.-Z. Zhang, L.-X. Wang, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

Umpolung addition of allyl-palladium intermediates to carbonyl electrophiles can be a useful alternative to the more classical allylation chemistry (see Review below). To date, there are very few examples which give products in high enantiomeric excess. This report describes the use of spiro-phosphite ligands to access enantiomerically enriched homoallylic alcohols using this strategy.

Review: G. Zanoni, A. Pontiroli, A. Marchetti, G. Vidari Eur. J. Org. Chem. 2007, 3599-3611.