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Brønsted Acid Catalyzed Asymmetric Propargylation of Aldehydes

2011; Wiley; Volume: 51; Issue: 6 Linguagem: Inglês

10.1002/anie.201107407

1521-3773

Pankaj Jain, Hao Wang, K. N. Houk, Jon C. Antilla,

Alkaloids: synthesis and pharmacology

Which gets activated? A versatile and highly enantioselective chiral Brønsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the chiral phosphoric acid activates the allenyl boronic acid pinacol ester reagent rather than the aldehyde. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.