Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 16, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202200371
Keywords
Atroposelectivity; Chiral N-N Axis; Enantiodivergence; Heterocycle; Organocatalysis
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Funding
- Ministry of Education of Singapore [A-0004103-00-00]
- National University of Singapore [A-0008372-00-00]
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We present a highly efficient method for the synthesis of axially chiral 1,1'-bipyrroles. The method involves the use of simple hydrazine and 1,4-diones as starting materials and further derivatization to obtain axially chiral bifunctional compounds with high potential in asymmetric catalysis.
We present herein a highly efficient atroposelective synthesis of axially chiral 1,1'-bipyrroles bearing an N-N linkage from simple hydrazine and 1,4-diones. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chrial phosphoric acid (CPA)-catalyzed double Paal-Knorr reaction, an intriguing Fe(OTf)(3)-induced enantiodivergence was also observed.
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