Chemical differentiation of enantiotopic groups: Diastereoselective opening of a prochiral dilactone

DOI: 10.1016/0040-4020(96)00863-0

Source and publish data:

Tetrahedron p. 14577 - 14598 (1996)

Update date:2022-08-04

Topics:

Authors:

Deseke, Eckart

Hoyer, Wolfgang

Winterfeldt, Ekkehard

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Article abstract of DOI:10.1016/0040-4020(96)00863-0

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.

Full text of DOI:10.1016/0040-4020(96)00863-0

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