Highly Regioselective Propargylation/Allenylation of Organolanthanum Reagents with Aldehydes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2023

Highly Regioselective Propargylation/Allenylation of Organolanthanum Reagents with Aldehydes

Résumé

The metal-mediated propargylation or allenylation of carbonyl compounds is well-adapted to the preparation of homopropargylic or allenylic alcohols, which are multifunctional intermediates in synthetic chemistry. However, the regioselectivity of reactions using propargyl or allenyl metal reagents is difficult to control, owing to the equilibrium between the two species. In our study, propargyl or allenyl organolanthanum reagents were prepared using trimethylsilylpropyne or prop-1-yn-1-ylbenzene substrates. The treatment of the organolanthanum reagents with aldehydes yielded the regioselective products, respectively. This study provides a better understanding of structural specificity and the special chemoselectivity of rare earth metal reagents.

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Chimie
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Dates et versions

hal-04284945 , version 1 (14-11-2023)

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Xue-Lin Dai, Jingdi Ran, Thayalan Rajeshkumar, Zhengping Xu, Shanshan Liu, et al.. Highly Regioselective Propargylation/Allenylation of Organolanthanum Reagents with Aldehydes. Organic Letters, 2023, 25 (17), pp.3060-3065. ⟨10.1021/acs.orglett.3c00824⟩. ⟨hal-04284945⟩
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