Development of a C2-Symmetric Chiral aza Spirocyclic Diol
- 17 April 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 22 (8), 3110-3113
- https://doi.org/10.1021/acs.orglett.0c00858
Abstract
A C-2-symmetric chiral spirocyclic diol aza-SPINOL containing a spirooxindole scaffold has been designed, synthesized, and optically resolved. The product could be synthesized on gram scale in an overall yield of 22%. Moreover, elaborations of aza-SPINOL to other chiral ligands as well as the preliminary investigation of the related bisphosphine ligand in the desymmet-rization of bisallylic amide were reported.Funding Information
- National Natural Science Foundation of China (21971263)
This publication has 30 references indexed in Scilit:
- Magical Chiral Spiro LigandsActa Chimica Sinica, 2014
- Design and Synthesis of Chiral Spiro LigandsJournal of Nepal Chemical Society, 2013
- Chiral Spiro CatalystsTopics in Organometallic Chemistry, 2011
- Development of Chiral Spiro Ligands for Metal-Catalyzed Asymmetric ReactionsBulletin of the Chemical Society of Japan, 2009
- Spiro Skeletons: A Class of Privileged Structure for Chiral Ligand DesignChemistry – An Asian Journal, 2008
- Chiral Diphosphine and Monodentate Phosphorus Ligands on a Spiro Scaffold for Transition-Metal-Catalyzed Asymmetric ReactionsAccounts of Chemical Research, 2008
- Highly efficient and practical resolution of 1,1′-spirobiindane-7,7′-diol by inclusion crystallization with N-benzylcinchonidinium chlorideTetrahedron: Asymmetry, 2002
- Monodentate Chiral Spiro Phosphoramidites: Efficient Ligands for Rhodium-Catalyzed Enantioselective Hydrogenation of EnamidesAngewandte Chemie, 2002
- Novel monodentate spiro phosphorus ligands for rhodium-catalyzed hydrogenation reactionsChemical Communications, 2002
- 1,1′-Spirobiindane-7,7′-diol: a novel, C2-symmetric chiral ligandTetrahedron: Asymmetry, 1999