Nickel-Catalyzed Enantioselective Reductive Spirocyclization of 1,6-Enynes with o-Bromobenzaldehydes

Haoyun Guo; Yate Chen; Wangqing Kong

doi:10.1055/a-2456-9530

Synthesis, Table of Contents

Synthesis 2025; 57(08): 1448-1456
DOI: 10.1055/a-2456-9530

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Nickel-Catalyzed Enantioselective Reductive Spirocyclization of 1,6-Enynes with o-Bromobenzaldehydes

Haoyun Guo‡

^aThe Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, P. R. of China

,

Yate Chen‡

^bCollege of Chemistry, Huazhong Agricultural University, Wuhan, 430070, P. R. of China

,

Wangqing Kong ∗

^aThe Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, P. R. of China

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Abstract

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Abstract

We developed a Ni-catalyzed asymmetric reductive spirocyclization of 1,6-enynes with o-haloaryl aldehydes. This approach provides an efficient method for the construction of chiral spiroindanone pyrrolidine derivatives in good yields with excellent enantio- and diastereoselectivity (up to 99% ee, >20:1 dr). This reaction does not require pre-prepared organometallic reagents and exhibits excellent substrate compatibility.

Key words

nickel catalysis - enantioselectivity - reductive spirocyclization - 1,6-enynes - spiroindanones

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References

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