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The gem-dialkyl effect has been used to promote the formation of functionalized gamma-lactones in the addition of benzenesulfonyl bromide to diene and enyne esters. Introduction of 3 mol % of pyridine into the reactions increases the yields of lactones produced from tertiary esters. Formation of the C(alpha)-C(beta) bond of gamma-lactones has been achieved in both C(alpha)-->C(beta) and C(beta)-->C(alpha) radical cyclization directions.
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Wang et al. (1999) studied this question.
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