4.7 Article

Synthesis of a Potential Intermediate for TMC-95A via an Organocatalyzed Aldol Reaction

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 19, Pages 9921-9928

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo4017315

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Funding

  1. Department of Chemistry, Case Western Reserve University

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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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