title: Remote Construction of Chiral Vicinal Tertiary and Quaternary Centers by Catalytic Asymmetric 1,6-Conjugate Addition of Prochiral Carbon Nucleophiles to Cyclic Dienones.
abstract: An unprecedented remote construction of chiral vicinal tertiary and quaternary centers by a catalytic asymmetric 1,6-conjugate addition of prochiral carbon nucleophiles to cyclic dienones has been developed. Both 5H-oxazol-4-ones and 2-oxindoles were found to be very efficient carbon nucleophiles in this reaction at a remote position, giving products with excellent enantio- and diastereoselectivities (up to 99% ee and >19:1 d.r. for 5H-oxazol-4-ones and up to 97% ee and >19:1 d.r. for 2-oxindoles).
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Yuan
authors.initials: Y
authors.lastname: Wei
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Zunwu
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Xinxin
authors.initials: X
authors.lastname: Wu
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Jie
authors.initials: J
authors.lastname: Fei
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Gu
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Xiaoqian
authors.initials: X
authors.lastname: Yuan
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China). yejx@ecust.edu.cn.
authors.forename: Jinxing
authors.initials: J
authors.lastname: Ye
keywords: 1,6-conjugate addition; amines; asymmetric catalysis; asymmetric synthesis; cyclic dienones; nucleophilic addition