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DOI: 10.1055/a-2275-3719
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Nickel-Catalyzed Asymmetric Borylative Coupling of 1,3-Dienes with Aldehydes

Jin-Tao Ma
,
Li-Jun Xiao∗
We thank the National Key R&D Program of China (2022YFA1503200), the National Natural Science Foundation of China (No. 22188101, 22201140), the Fundamental Research Funds for the Central Universities, and the Haihe Laboratory of Sustainable Chemical Transformations for financial support.
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Abstract

The nickel-catalyzed borylative coupling of aldehydes and 1,3-dienes with diboron reagents offers an efficient method for synthesizing valuable homoallylic alcohols from easily accessible starting materials. However, achieving enantioselectivity in this reaction has been a significant challenge. We discuss our recent report on the first example of a nickel-catalyzed enantioselective borylative coupling of aldehydes with 1,3-dienes, employing a chiral spiro-phosphine–oxazoline ligand. Notably, by utilizing (E)-1,3-dienes or (Z)-1,3-dienes, we can reverse the diastereoselectivity, yielding either anti- or syn-products, respectively.

Key words

borylative coupling - homoallylic alcohols - nickel catalysis - spiro compound - enantioselectivity - diastereoselectivity


Publication History

Received: 30 November 2023

Accepted after revision: 23 February 2024

Accepted Manuscript online:
23 February 2024

Article published online:
13 March 2024

© 2024. Thieme. All rights reserved

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