title: Organocatalytic diversity-oriented asymmetric synthesis of tricyclic chroman derivatives.
abstract: The tandem oxo-Michael-IED/HDA and oxo-Michael-IED/HDA-Michael-Aldol condensation transformations between (E)-2-hydroxyaryl-2-oxobut-3-enoate derivatives with enals have been developed in the presence of (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst. Two types of tricyclic chroman derivatives were, respectively, obtained, by adjusting the reactant ratio and reaction temperature, in good yields (up to 96%) with excellent enantioselectivities (up to >99%) and good diastereoselectivities (up to >30/1). It should be noted that the divergent chiral chroman derivatives were obtained by successive reaction of (E)-2-hydroxyaryl-2-oxobut-3-enoate derivatives with two different enal substrates in highly catalytic results.
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou 215123, People's Republic of China.
authors.forename: Zhi-Cong
authors.initials: ZC
authors.lastname: Geng
authors.forename: Shao-Yun
authors.initials: SY
authors.lastname: Zhang
authors.forename: Nai-Kai
authors.initials: NK
authors.lastname: Li
authors.forename: Ning
authors.initials: N
authors.lastname: Li
authors.forename: Jian
authors.initials: J
authors.lastname: Chen
authors.forename: Hai-Yan
authors.initials: HY
authors.lastname: Li
authors.forename: Xing-Wang
authors.initials: XW
authors.lastname: Wang
mesh_terms: D002087:Butyrates / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D002087:Butyrates; D002839:Chromans; D004987:Ethers; D011759:Pyrrolidines; D014297:Trimethylsilyl Compounds; C575987:diphenylprolinol; C000599343:diphenylprolinol trimethylsilyl ether