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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
Abstract 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.