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

Barozzino Consiglio, Gabriella;Yuan, Yi;Fressigné, Catherine;Harrison-Marchand, Anne;Maddaluno, Jacques;et.al.
(2015) Organometallics — Vol. 34, n° 18, p. 4441-4450 (2015)

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Abstract
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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Barozzino Consiglio, G., Yuan, Y., Fressigné, C., Harrison-Marchand, A., Oulyadi, H., & Maddaluno, J. (2015). Enantioselective Alkynylation of Aldehydes by Mixed Aggregates of 3-Aminopyrrolidine Lithium Amides and Lithium Acetylides. Organometallics, 34(18), 4441-4450. https://doi.org/10.1021/acs.organomet.5b00647 (Original work published 2015)