Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1‑Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins

Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1‑Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins

A chiral squaramide catalyzed approach constructing spiro-3,4-dihydrocoumarin motif by the enantioselective 1,6-addition/acetalization reactions of 1-oxotetralin-2-carbaldehydes and ortho-hydroxyphenyl-substituted para-quinone methides followed by an oxidation was developed. The reactions proceeded...

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Veröffentlicht in:Journal of organic chemistry 2018-03, Vol.83 (5), p.2714-2724
Hauptverfasser: Zhang, Zhi-Pei, Chen, Li, Li, Xin, Cheng, Jin-Pei
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Chen, Li
Li, Xin
Cheng, Jin-Pei
description A chiral squaramide catalyzed approach constructing spiro-3,4-dihydrocoumarin motif by the enantioselective 1,6-addition/acetalization reactions of 1-oxotetralin-2-carbaldehydes and ortho-hydroxyphenyl-substituted para-quinone methides followed by an oxidation was developed. The reactions proceeded smoothly with a wide range of p-QMs and 1-oxotetralin-2-carbaldehydes to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee).
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title Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1‑Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins
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