trans-Substituted γ-lactones are formed with high diastereoselectivity according to Equation (a), especially when cuprates are used as organometallic reagents. For allyltrimethylsilane/TiCl4, the selectivity is only large when R1 is a bulky group. The γ-lactones thus obtained are valuable synthetic intermediates, and their formation is of mechanistic interest since they can be used to test the validity of the Felkin–Ahn model (R1 = Me, iPr, Ph; R2 = Me, nBu, allyl).
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Kunz et al. (1988) studied this question.
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