Catalytic Asymmetric Prins Bicyclization for the  endo ‐Selective Formation of 2,6‐dioxabicyclo[2.2.2]octanes | Zendy

Liu Jie | Zendy; Zhou Lijun | Zendy; Wang Chao | Zendy; Liang Demin | Zendy; Li Zhiming | Zendy; Zou Yue | Zendy; Wang Quanrui | Zendy; Goeke Andreas | Zendy

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Catalytic Asymmetric Prins Bicyclization for the endo ‐Selective Formation of 2,6‐dioxabicyclo[2.2.2]octanes

Author(s) -

Liu Jie,

Zhou Lijun,

Wang Chao,

Liang Demin,

Li Zhiming,

Zou Yue,

Wang Quanrui,

Goeke Andreas

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201600847

Subject(s) - catalysis , chemistry , glyoxylate cycle , bicyclic molecule , organic chemistry , combinatorial chemistry , stereochemistry , enzyme

A new Lewis acid‐catalyzed endo ‐selective Prins bicyclization of γ,δ‐unsaturated aldehydes or ketones with a broad range of aldehydes to dioxabicyclo[2.2.2]octanes is disclosed. When using a chiral BINOL‐derived N ‐triflylphosphoramide (NTPA) as catalyst and glyoxylate esters as substrates, the cross‐dimerization afford functionalized bicyclic acetals with excellent diastereo‐ and enantioselectivities.

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