A New Family of Cinchona-Derived Bifunctional Asymmetric Phase-Transfer Catalysts: Application to the Enantio- and Diastereoselective Nitro-Mannich Reaction of Amidosulfones

作者：Johnson Kayli M; Rattley Matt S; Sladojevich Filippo; Barber David M; Nunez Marta G; Goldys Anna M; Dixon Darren J^*

来源：Organic Letters, 2012, 14(10): 2492-2495.

DOI：10.1021/ol300779x

A new family of bifunctional H-bond donor phase-transfer catalysts derived from cinchona alkaloids has been developed and evaluated in the enantio- and diastereoselective nitro-Mannich reaction of in situ generated N-Boc-protected imines of aliphatic, aromatic, and heteroaromatic aldehydes. Under optimal conditions, good reactivity and high diastereoselectivities (up to 24:1 dr) and enantioselectivities (up to 95% ee) were obtained using a 9-amino-9-deoxyepiquinidine-derived phase-transfer catalyst possessing a 3,5-bis(trifluoromethyl)phenylurea H-bond donor group at the 9-position.

• 出版日期2012-5-18