title: Organocatalytic Asymmetric Tandem Nazarov Cyclization/Semipinacol Rearrangement: Rapid Construction of Chiral Spiro[4.4]nonane-1,6-diones.
abstract: A novel organocatalytic asymmetric tandem Nazarov cyclization/semipinacol rearrangement reaction using "unactivated" substrates has been developed, generating a series of chiral spiro[4.4]nonane-1,6-diones in up to 96% yield and 97% enantiomeric excess. Significantly, it is the first direct example for asymmetric synthesis of cyclopentanones with four stereocenters using Nazarov cyclization. DFT calculations have been applied to understand the reaction mechanism, stereochemistry, and substituent effects.
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.|§Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. China.
authors.forename: Bin-Miao
authors.initials: BM
authors.lastname: Yang
authors.affiliation: ‡Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. China.
authors.forename: Pei-Jun
authors.initials: PJ
authors.lastname: Cai
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.|§Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. China.
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.affiliation: ‡Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. China.
authors.forename: Zhi-Xiang
authors.initials: ZX
authors.lastname: Yu
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.|§Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. China.
authors.forename: Zhi-Min
authors.initials: ZM
authors.lastname: Chen
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.|§Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. China.
authors.forename: Shuang-Hu
authors.initials: SH
authors.lastname: Wang
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.|§Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. China.
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Wang
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.|§Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. China.
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang