Base Promoted Rearrangement of Carbonate Esters Derived from Aldehyde Cyanohydrins: Application to the Synthesis of α-Keto Esters
- 1 June 1990
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 20 (12), 1831-1836
- https://doi.org/10.1080/00397919008053107
Abstract
Acylation of the cyanohydrin derivative (2) of representative aldehydes with ethyl chloroformate, followed by treatment of the corresponding mixed carbonate esters (3) with lithium hexamethyldisilazide, afforded the cyanohydrin derivative (4) of α-keto esters. Cleavage of the latter (4) with 2,6-lutidine in the presence of silver nitrate led to the procurement of α-keto esters in >50% overall yield.Keywords
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