title: Asymmetric catalytic conjugate addition of acetaldehyde to nitrodienynes/nitroenynes: applications to the syntheses of (+)-α-lycorane and chiral β-alkynyl acids.
abstract: The catalytic enantioselective conjugate addition of acetaldehyde to polyconjugated substrates, nitrodienynes and nitroenynes, has been accomplished using organocatalysis. Various functionalized 1,3-enynes and propargylic compounds were obtained in moderate to good yields with high enantioselectivity. The synthetic utilities of the conjugate addition reactions have been highlighted in the concise total synthesis of (+)-α-lycorane and the metal-free synthesis of chiral β-alkynyl acids.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming, Yunnan 650091, P. R. China.
authors.forename: Xue-Ling
authors.initials: XL
authors.lastname: Meng
authors.forename: Teng
authors.initials: T
authors.lastname: Liu
authors.forename: Zhong-Wen
authors.initials: ZW
authors.lastname: Sun
authors.forename: Jin-Chen
authors.initials: JC
authors.lastname: Wang
authors.forename: Fang-Zhi
authors.initials: FZ
authors.lastname: Peng
authors.forename: Zhi-Hui
authors.initials: ZH
authors.lastname: Shao
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D047151:Amaryllidaceae Alkaloids; D009574:Nitro Compounds; C412290:lycorane; D000079:Acetaldehyde