Direct Organocatalytic Mannich Reaction of Acetaldehyde: An Improved Catalyst and Mechanistic Insight from a Computational Study

Abstract

A chiral diaryl prolinol silyl ether organocatalyst with an acid is used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in good yields and with excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically. 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.