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Synlett 1998; 1998(1): 93-95
DOI: 10.1055/s-1998-1573
DOI: 10.1055/s-1998-1573
letter
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The Generation of Highly Functionalized Organometallics via Organotellurides and The Stereospecific Preparation of N-Isobutyl 6-Hydroxyl-(2E,4Z)-hexadienamide Derivatives
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Publication History
Publication Date:
31 December 2000 (online)
The dilithiation of N-isobutyl 5-telluro-(2E,4Z)-pentadienamide 3 with n-butyl lithium in Trapp mixture at ca. -100 °C leads to the corresponding N-lithium N-isobutyl 5-lithio-(2E,4Z)-hexadienamide 5, which could be converted into the corresponding cerium reagent 7. Both of the highly functionalized organometallics react with carbonyl compounds to afford the corresponding pure N-isobutyl 6-hydroxyl-(2E,4Z)-hexadienamide derivatives in good yields.
dienyltelluride - tellurium-lithium exchange reaction - highly functionalized organometallics - carbonyl addition