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Diastereoselective 1,4-Conjugate Addition of Alkyl Cuprates to Methyl Cyclopent-1-enecarboxylates

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journal contribution
posted on 21.02.2018, 12:50 by Staffan Karlsson, Philip Cornwall, Angéle Cruz, Fritiof Pontén, Maria Fridén-Saxin, Andrew Turner
Starting from readily available homochiral Vince lactam, trisubstituted cyclopentanes were obtained utilizing conjugate addition of alkyl cuprates as an efficient approach to introduce different side chains. Although the 1,4-conjugate addition reactions gave the products as mixtures of diastereomers, an epimerization approach followed by crystallization furnished the stereoisomerically pure cyclopentanes.

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