Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 14, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202117340
Keywords
Axially Chiral Aldehydes; Desymmetrization; Esterification; Kinetic Resolution; N-Heterocyclic Carbenes
Categories
Funding
- NSFC [21831002, 22001157, 22193012]
- Ten Thousand Talents Program
- Fundamental Research Funds for the Central Universities [2412021QD007]
- Natural Science Foundation of Shaanxi Province [2020JQ-404]
Ask authors/readers for more resources
In this research, an NHC-catalyzed atroposelective esterification of biaryl dialdehydes is described as a general and practical strategy for the construction of axially chiral aldehydes. The method features excellent enantioselectivity, mild conditions, good functional-group tolerance, and applicability to late-stage functionalization.
Axially chiral aldehydes have received increasing attention in enantioselective catalysis. However, only very few catalytic methods have been developed to construct structurally diverse axially chiral aldehydes. We herein describe an NHC-catalyzed atroposelective esterification of biaryl dialdehydes as a general and practical strategy for the construction of axially chiral aldehydes. Mechanistic studies indicate that coupling proceeds through a novel combination of NHC-catalyzed desymmetrization of the dialdehydes and kinetic resolution. This protocol features excellent enantioselectivity, mild conditions, good functional-group tolerance, and applicability to late-stage functionalization and provides a modular platform for the synthesis of axially chiral aldehydes and their derivatives.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available