Back to Search
Start Over
Design and Synthesis of Spirochroman‐2‐on‐4,1'‐indan‐7'‐ol and Its Application for Synthesizing Chiral Monophosphinite Ligands†.
- Source :
- Chinese Journal of Chemistry; Nov2023, Vol. 41 Issue 22, p2988-2994, 7p
- Publication Year :
- 2023
-
Abstract
- Comprehensive Summary: The design and synthesis of spirochroman‐2‐on‐4,1'‐indan‐7'‐ol (SCIOL) and its application for synthesizing chiral monophosphinite ligands are reported. The synthesis features a tandem double Friedel‐Crafts reaction/lactonization to construct the spiro framework and the desired racemic SCIOL was obtained via 6 steps with a total yield of 44.5%. Using an inclusion resolution with N‐benzylcinchonidinium chloride, the optical SCIOL could be obtained in good yields on a gram scale. The preliminary studies indicated that the corresponding chiral spiro monophosphinite ligands exhibit high catalytic activity and enantioselectivity (up to 94% ee) in the rhodium‐catalyzed asymmetric hydrogenation of N‐acetyl dehydroamino esters. These outcomes highlight the significant potential of SCIOL as a useful framework for the development of chiral spiro ligands. [ABSTRACT FROM AUTHOR]
- Subjects :
- HYDROGENATION
FRIEDEL-Crafts reaction
CATALYTIC activity
LIGANDS (Chemistry)
Subjects
Details
- Language :
- English
- ISSN :
- 1001604X
- Volume :
- 41
- Issue :
- 22
- Database :
- Complementary Index
- Journal :
- Chinese Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 173013855
- Full Text :
- https://doi.org/10.1002/cjoc.202300319