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Synthesis of a potential intermediate for TMC-95A via an organocatalyzed aldol reaction
Anthony J Pearson1, Santanu Panda, Scott D Bunge
1Department of Chemistry, Case Western Reserve University , Cleveland, Ohio 44106, United States.
Abstract:
N-Prolinylanthranilamide-based pseudopeptide organocatalyst 14 was shown to promote enantioselective direct aldol reaction of 7-iodoisatin and 2,2-dimethyl-1,3-dioxan-5-one with 90% conversion (75% isolated yield), 90% enantioselectivity, and 23:1 diastereoselectivity. To demonstrate the synthetic utility of this chemistry, the racemic aldol reaction product was converted in five steps to a potential intermediate for construction of the natural product TMC-95A.
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