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 |
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Keywords
- 1,4-addition
- allylic alkylation
- chiral ligands
- paracyclophanes
- phosphites
- planar chirality
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands. / Shibata, Takanori; Fukai, Miku; Sekine, Ryosuke; Hazra, Madhurima; Kanyiva, Stephen Kyalo.
In: Synthesis (Germany), Vol. 48, No. 16, ss-2016-c0168-st, 16.08.2016, p. 2664-2670.Research output: Contribution to journal › Review article
}
TY - JOUR
T1 - Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands
AU - Shibata, Takanori
AU - Fukai, Miku
AU - Sekine, Ryosuke
AU - Hazra, Madhurima
AU - Kanyiva, Stephen Kyalo
PY - 2016/8/16
Y1 - 2016/8/16
N2 - 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.
AB - 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.
KW - 1,4-addition
KW - allylic alkylation
KW - chiral ligands
KW - paracyclophanes
KW - phosphites
KW - planar chirality
UR - http://www.scopus.com/inward/record.url?scp=84978964186&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84978964186&partnerID=8YFLogxK
U2 - 10.1055/s-0035-1562097
DO - 10.1055/s-0035-1562097
M3 - Review article
AN - SCOPUS:84978964186
VL - 48
SP - 2664
EP - 2670
JO - Synthesis (Germany)
JF - Synthesis (Germany)
SN - 0039-7881
IS - 16
M1 - ss-2016-c0168-st
ER -