title: An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,β-unsaturated aldehydes with unusual regioselectivity.
abstract: An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,β-unsaturated aldehydes was developed. Bicyclo[3.3.1]nonanone products were obtained with good yields and excellent enantioselectivities. The reaction occurred with unusual regioselectivity. A dienolate-iminium activation mechanism was proposed. The products were transformed to eight-membered cyclic ketones with high enantioselectivity.
authors: College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China. xuanyn@mail3.sysu.edu.cn.
authors: Yi-ning
authors: YN
authors: Xuan
authors: Zhen-yu
authors: ZY
authors: Chen
authors: Ming
authors: M
authors: Yan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C533398:2-nitrocyclohexanone; D000447:Aldehydes; D001643:Bridged Bicyclo Compounds; D003512:Cyclohexanones; D007097:Imines; D007659:Ketones