title: Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile.
abstract: 2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities. Moreover, this reaction can be performed in up to 6 mmol scale without any noticeable loss of yield and stereoselectivity.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China. hanzy2014@ustc.edu.cn.
authors.forename: Alafate
authors.initials: A
authors.lastname: Adili
authors.forename: Zhong-Lin
authors.initials: ZL
authors.lastname: Tao
authors.forename: Dian-Feng
authors.initials: DF
authors.lastname: Chen
authors.forename: Zhi-Yong
authors.initials: ZY
authors.lastname: Han
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011803:Quinine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D045563:Indolequinones; D009570:Nitriles; C068040:quinone methide; D011803:Quinine; C000945:dicyanmethane