Abstract
Various planar-chiral 1,n-dioxa[n]paracyclophanes possessing a phenolic hydroxyl group have been synthesized via enantioselective ortho-lithiation. Subsequent reaction with 2,2′-biarylene phosphorochloridites gave a new family of chiral phosphites. These phosphites were then used as chiral ligands in the enantioselective palladium-catalyzed allylic alkylation of dimethyl malonate with (E)-1,3-diphenylallyl acetate and the rhodium-catalyzed 1,4-addition of phenylboronic acid to cyclohex-2-enone.
| Original language | English |
|---|---|
| Article number | ss-2016-c0168-st |
| Pages (from-to) | 2664-2670 |
| Number of pages | 7 |
| Journal | Synthesis (Germany) |
| Volume | 48 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 2016 Aug 16 |
Keywords
- 1,4-addition
- allylic alkylation
- chiral ligands
- paracyclophanes
- phosphites
- planar chirality
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Shibata, T., Fukai, M., Sekine, R., Hazra, M., & Kanyiva, S. K. (2016). Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands. Synthesis (Germany), 48(16), 2664-2670. [ss-2016-c0168-st]. https://doi.org/10.1055/s-0035-1562097