Manganese-catalyzed cyclopropanation of allylic alcohols with sulfones

Ke Yu, Qin Nie, Qianjin Chen and Weiping Liu ()
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Ke Yu: Donghua University
Qin Nie: Donghua University
Qianjin Chen: Donghua University
Weiping Liu: Donghua University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Cyclopropanes are among the most important structural units in natural products, pharmaceuticals, and agrochemicals. Herein, we report a manganese-catalyzed cyclopropanation of allylic alcohols with sulfones as carbene alternative precursors via a borrowing hydrogen strategy under mild conditions. Various allylic alcohols and arylmethyl trifluoromethyl sulfones work efficiently in this borrowing hydrogen transformation and thereby deliver the corresponding cyclopropylmethanol products in 58% to 99% yields. Importantly, a major benefit of this transformation is that the versatile free alcohol moiety is retained in the resultant products, which can undergo a wide range of downstream transformations to provide access to a series of functional molecules. Mechanistic studies support a sequential reaction mechanism that involves catalytic dehydrogenation, Michael addition, cyclization, and catalytic hydrogenation.

Date: 2024
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DOI: 10.1038/s41467-024-51188-x

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