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

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• 作者：Gabriella Barozzino-Consiglio ; Yi Yuan ; Catherine Fressign茅 ; Anne Harrison-Marchand ; Hassan Oulyadi ; Jacques Maddaluno
• 刊名：Organometallics
• 出版年：2015
• 出版时间：September 28, 2015
• 年：2015
• 卷：34
• 期：18
• 页码：4441-4450
• 全文大小：514K
• ISSN：1520-6041

文摘

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鈥揕i鈥揅鈥揕i 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 鈭?8 掳C.