Static to inducibly dynamic stereocontrol: The convergent use of racemic b-substituted ketones

Jacob S. DeHovitz, Yong Yao Loh, Jacob A. Kautzky, Kazunori Nagao, Andrew J. Meichan, Motoshi Yamauchi, David W.C. MacMillan, Todd K. Hyster

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The synthesis of stereochemically complex molecules in the pharmaceutical and agrochemical industries requires precise control over each distinct stereocenter, a feat that can be challenging and time consuming using traditional asymmetric synthesis. Although stereoconvergent processes have the potential to streamline and simplify synthetic routes, they are currently limited by a narrow scope of inducibly dynamic stereocenters that can be readily epimerized. Here, we report the use of photoredox catalysis to enable the racemization of traditionally static, unreactive stereocenters through the intermediacy of prochiral radical species. This technology was applied in conjunction with biocatalysts such as ketoreductases and aminotransferases to realize stereoconvergent syntheses of stereodefined g-substituted alcohols and amines from b-substituted ketones.

Original languageEnglish (US)
Pages (from-to)1113-1118
Number of pages6
JournalScience
Volume369
Issue number6507
DOIs
StatePublished - Aug 28 2020

All Science Journal Classification (ASJC) codes

  • General

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