Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 50, Pages 16561-16566Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b11435
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Funding
- National Natural Science Foundation of China [21572095, 21602097]
- Shenzhen special funds for the development of biomedicine, Internet, new energy, and new material industries [JCYJ20150430160022510]
- Thousand Young Talents Program
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Axially chiral 1,1'-spirobiindane-7,7'-diol (SPINOL) is the most fundamental and important privileged structure from which other chiral ligands containing a 1,1'-spirobiindane backbone are synthesized. Driven by the development of enantioselective syntheses of axially chiral SPINOL derivatives, we have successfully developed the first phosphoric acid-catalyzed asymmetric approach. This approach is highly convergent and functional group tolerant, efficiently providing SPINOLs in good yield with excellent enantioselectivity, thus delivering a practical and straightforward access to this privileged structure. It should be emphasized that the catalyst loading could be decreased to only 0.1 mol% for the preparative-scale synthesis. Furthermore, 4,4'-dimethyl-SPINOL-phosphoric acid was synthesized and applied to catalyze the model reaction for synthesis of enantioenriched SPINOL derivatives.
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