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- Title
Design and Synthesis of Spirochroman‐2‐on‐4,1'‐indan‐7'‐ol and Its Application for Synthesizing Chiral Monophosphinite Ligands<sup>†</sup>.
- Authors
Zhang, Yang‐Ming; Guo, Shu‐Min; Wang, Qing‐Xian; Zheng, Xiao‐Jie; Xie, Jian‐Hua; Zhou, Qi‐Lin
- 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.
- Subjects
HYDROGENATION; FRIEDEL-Crafts reaction; CATALYTIC activity; LIGANDS (Chemistry)
- Publication
Chinese Journal of Chemistry, 2023, Vol 41, Issue 22, p2988
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202300319