Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 26, Pages 8064-8068Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b03642
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Funding
- SUSTech
- Science and Technology Innovation Committee of Shenzhen [JCYJ20170817105056467, JCYJ20170817110055425]
- SUSTech - Science and Technology Innovation Committee of Shenzhen [KQTD20150717103157174]
- National Natural Science Foundation of China [21432007]
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We herein present a facile and column-free synthetic route toward a structurally unique oxa-spirocyclic diphenol, termed as O-SPINOL. Features of the synthesis include the construction of the all-carbon quaternary center at an early stage, a key double intramolecular SNAr step to introduce the spirocycles and the feasibility of operating on >100 g scale. Both enantiomers of O-SPINOL can be easily accessed through optical resolution with L-proline by control of the solvent. The chiral tridentate ligand O-SpiroPAP derived from O-SPINOL has been successfully synthesized and applied in the iridium-catalyzed asymmetric hydrogenation of bridged biaryl lactones under mild reaction conditions, providing valuable and enantioenriched axially chiral molecules in excellent yields and enantioselectivities (up to 99% yield and >99% ee). This method represents a rare example of constructing axially chiral molecules by direct reduction of esters with H-2.
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