Tetrahedron p. 14577 - 14598 (1996)
Update date:2022-08-04
Topics:
Deseke, Eckart
Hoyer, Wolfgang
Winterfeldt, Ekkehard
Prochiral dilactone 1 has been synthesized and subjected to diastereoselective nucleophilic opening. The structural features of chiral, enantiomerically pure nucleophiles have been optimized regarding their capability to perform prochiral recognition at dilactone 1. 3-Ketoglutaric mono acid products 2 of dilactone opening, which are versatile building blocks for natural product synthesis, have been obtained in diastereomeric ratios up to 84:16 and were enriched by subsequent crystallization to 97.5:2.5.
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