A 4??Hydroxypyrrolidine??Catalyzed Mannich Reaction of Aldehydes: Control of anti??Selectivity by Hydrogen Bonding Assisted by Brønsted Acids

E Gómez??Bengoa, M Maestro, A Mielgo…

Index: Gomez-Bengoa, Enrique; Maestro, Miguel; Mielgo, Antonia; Otazo, Itziar; Palomo, Claudio; Velilla, Irene Chemistry - A European Journal, 2010 , vol. 16, # 18 p. 5333 - 5342

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Citation Number: 21

Abstract

Abstract An anti-selective Mannich reaction of aldehydes with N-sulfonyl imines has been developed by using a 4-hydroxypyrrolidine in combination with an external Brønsted acid. The catalyst design is based on three elements: the α-substituent of the pyrrolidine, the 4- hydroxy group, and the Brønsted acid, the combination of which is essential for high chemical and stereochemical efficiency. The reaction works with aromatic aldehyde- ...