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0003961355
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For an excellent discussion of related alkylations with chiral organolithiums see: J. Clayden Organolithiums: Selectivity for Synthesis 2002 Pergamon Amsterdam Chapter 6
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For the electrophile-dependent alkylations of a related, but cyclic, nitrile see: F.F. Fleming, Z. Zhang, G. Wei, and O.W. Steward J. Org. Chem. 71 2006 1430
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The hydroxynitriles were prepared by condensing the appropriate lithiated nitrile with an epoxide
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4444350585
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4Cl was added, followed after 20 min, by an aqueous solution of 2 M HCl. The latter modification prevents cyclization to the corresponding lactone
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33644924126
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Prior to the deprotonation, the molarity of i-PrMgCl was determined by titration
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Cyclic alkylmagnesium alkoxides react selectively with benzaldehyde, whereas 5 reacts non-selectively, but are not reactive toward activated allylic or benzylic halides unless in the presence of HMPA
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18744386169
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®
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® F. Antoneitti, E. Brenna, C. Fuganti, F.G. Gatti, T. Giovenzana, V. Grande, and L. Malpezzi Synthesis 2005 1148
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24044527853
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The procedure is described in Supplementary data SI51
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