title: Asymmetric synthesis of 3,4-diaminochroman-2-ones promoted by guanidine and bisguanidium salt.
abstract: A highly enantioselective synthesis of 3,4-diaminochroman-2-ones has been realized via the domino reaction of o-hydroxy aromatic aldimines and azlactones. Notably, a cis-product was obtained as the major product by the use of guanidine 2a whereas a trans-product was the major product with bisguanidium salt 3•HBAr(F)(4). In two cases, various substituted 3,4-dihydrocoumarins were obtained with high yields (up to 99%) as well as excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >99:1 cis:trans and 98:2 trans:cis, respectively) under mild reaction conditions.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
authors.forename: Shunxi
authors.initials: S
authors.lastname: Dong
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Yulong
authors.initials: Y
authors.lastname: Zhang
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis*; D019791:Guanidine / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002839:Chromans; D012492:Salts; D019791:Guanidine