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Rh(i)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates

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Abstract

An asymmetric intermolecular [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates, which was catalyzed by a rhodium(I)–chiral phosphoramidite complex, was developed. This protocol provided a highly enantioselective access to prepare carbonyl substituted cyclohexa-1,4-dienes with up to 96% yield and >99% ee. Notably, a cycloaddition on the 10 g scale gave the product in 92% yield and with 99% ee, which showed great potential for the scale-up synthesis of carbonyl substituted cyclohexa-1,4-dienes. In addition, oxidative aromatizations and hydrolysis of the products were also investigated.

Graphical abstract: Rh(i)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates

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Article information


Submitted
19 Feb 2020
Accepted
19 Mar 2020
First published
19 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Rh(I)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates

R. L. Bao, J. Yin, L. Shi and L. Zheng, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00361A

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