Journal of Organic Chemistry p. 5343 - 5346 (1994)
Update date:2022-09-26
Topics:
Solladie-Cavallo, Arlette
Csaky, Aurelio G.
Gantz, Ingo
Suffert, Jean
It is shown that monoalkylation of 8-phenylmenthyl phenylacetate using lithiated bases leads to poor or no diastereoselectivities (50/50 to 69/31) and high yields (75 to 98percent) while alkylation using tBu-P4 (a strong and cation free base, known to provide "naked" anion) leads to high diastereoselectivities (92/8 to 98/2) and high yields (65 to 95percent).It is postulated that, in the case of phenylacetates, the degree of aggregation of the lithium enolate is responsible of the poor diastereoselectivities.
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Doi:10.1021/ol500744k
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