Enantioselective Alkynylation of Aldehydes by Mixed Aggregates of 3-Aminopyrrolidine Lithium Amides and Lithium Acetylides - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organometallics Année : 2015

Enantioselective Alkynylation of Aldehydes by Mixed Aggregates of 3-Aminopyrrolidine Lithium Amides and Lithium Acetylides

Résumé

Lithium acetylides form, with 3-aminopyrrolidine lithium amides, noncovalent 1/1 mixed aggregates that have been characterized by 1D and 2D multinuclear NMR spectroscopy and DFT computations. The results show that the complex adopts a structure organized around a N–Li–C–Li core and that the acetylide appendage lies within the plane of this quadrilateral, midway between the two lithium cations. These complexes have been employed for the enantioselective alkynylation of a series of aromatic aldehydes and provided the expected propargylic alcohols in ee values up to 85% in THF at −78 °C.

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Chimie organique
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Dates et versions

hal-02019204 , version 1 (14-02-2019)

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Gabriella Barozzino-Consiglio, Yi Yuan, Catherine Fressigné, Anne Harrison-Marchand, Hassan Oulyadi, et al.. Enantioselective Alkynylation of Aldehydes by Mixed Aggregates of 3-Aminopyrrolidine Lithium Amides and Lithium Acetylides. Organometallics, 2015, 34 (18), pp.4441-4450. ⟨10.1021/acs.organomet.5b00647⟩. ⟨hal-02019204⟩
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