Diastereoselective 1,4-Conjugate Addition of Alkyl Cuprates to Methyl Cyclopent-1-enecarboxylates,Organic Process Research & Development

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Diastereoselective 1,4-Conjugate Addition of Alkyl Cuprates to Methyl Cyclopent-1-enecarboxylates
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-02-21 00:00:00 , DOI: 10.1021/acs.oprd.7b00374
Staffan Karlsson ₁ , Philip Cornwall ₂ , Angéle Cruz ₁ , Fritiof Pontén ₁ , Maria Fridén-Saxin ₃ , Andrew Turner ₂

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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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