Tetrahedron p. 4189 - 4194 (1981)
Update date:2022-08-29
Topics:
Dubois, Jacques-Emile
Zhang, Ben Li
Lion, Claude
The synthesis of tBu2MeCCOOH, which is among the most sterically hindered known acids is described.Only Newman's sequence via tBu2C=O, tBu2MeCOH, tBu2C=CH2, tBu2CHCH2OH, tBu2CHCOOH, tBu2CHCOCl and tBu2C=C=O, which has been optimized in this work by a direct access to tBu2CHCOOH, permits the preparation of tBu2MeCCOOH.The condensation of the corresponding chloride with a Grignard reagent yields new highly-hindered ketones tBu2MeCCOR wich by alkylation give more substituted structures.The limitations of each method have been studied in this work.
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