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- Title
Scalable, Stereocontrolled Formal Syntheses of (+)‐Isoschizandrin and (+)‐Steganone: Development and Applications of Palladium(II)‐Catalyzed Atroposelective C−H Alkynylation.
- Authors
Liao, Gang; Yao, Qi‐Jun; Zhang, Zhuo‐Zhuo; Wu, Yong‐Jie; Huang, Dan‐Ying; Shi, Bing‐Feng
- Abstract
Abstract: Dibenzocyclooctadiene lignans are an interesting class of molecules because of their unique structure based on an axially chiral biaryl moiety as well as their significant biological activity. Herein, we describe the development of a palladium‐catalyzed atroposelective C−H alkynylation and its application in gram‐scale, stereocontrolled formal syntheses of (+)‐isoschizandrin and (+)‐steganone. <italic>tert</italic>‐Leucine was identified as an efficient, catalytic transient chiral auxiliary. A wide range of enantiomerically enriched biaryl compounds were prepared by this approach in good yields (up to 99 %) with excellent enantioselectivity (up to >99 % <italic>ee</italic>).
- Subjects
PALLADIUM catalysts; CARBON-hydrogen bonds; CYCLOOCTADIENE; LIGNANS; FUNCTIONAL groups; CHEMICAL yield
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 14, p3723
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201713106