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August 23, 2025

Axial‐to‐Point Chirality Transfer: Chromium(VI)‐Catalyzed Hydroxylative Dearomatization of 2‐Naphthols

Key Points

Chromium(VI) catalysis achieves enantioselective hydroxylative dearomatization of 2-naphthols, producing high yields up to 85%.
The transformation highlights excellent enantioselectivities above 99% ee as well as enantiospecificity exceeding 99% es, showcasing its efficiency.
This approach utilizes axial-to-point chirality transfer, advancing methods to construct chiral centers from axially chiral compounds.
The findings may enable new strategies for synthesis in organic chemistry, expanding the range of stable chiral reagents available.

Abstract

Axial‐to‐point chirality transfer is an important strategy for the construction of chiral centers, where the axial chiral reagents are mostly limited to atropomerically stable ones. In this work, a Cr(VI)‐catalyzed enantioselective hydroxylative dearomatization (via axial‐to‐point chirality transfer) of axially chiral 2‐naphthols is presented. This transformation proceeds efficiently across a broad range of axially chiral 2‐naphthols, yielding hydroxylative dearomatized products in good yields (up to 85%) with excellent enantioselectivities (up to > 99% ee) and enantiospecificity (up to > 99% es).

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Axial‐to‐Point Chirality Transfer: Chromium(VI)‐Catalyzed Hydroxylative Dearomatization of 2‐Naphthols

Key Points

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