Abstract
A proline-derived aminohydroxyphosphine ligand induced excellent regio- and enantiose-lectivities (SN2′: SN2>94:6, 94-97% ee) in the copper-catalyzed substitution reaction of cinnamyl phosphates with Et2Zn. A computational modelling study of the reaction pathway suggests that the displacement of the leaving group takes place in an ordered, anti-fashion through simultaneous copper-olefin and zinc-oxygen interactions, which is critical for the enantioselection.
Original language | English |
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Pages (from-to) | 1014-1018 |
Number of pages | 5 |
Journal | Advanced Synthesis and Catalysis |
Volume | 351 |
Issue number | 7-8 |
DOIs | |
Publication status | Published - 2009 May |
Externally published | Yes |
Keywords
- Allylic substitution
- C-C bond formation
- Copper
- Organozinc reagents
- Phosphane ligands
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry