Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 31, Pages 9217-9221Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705539
Keywords
antibiotics; asymmetric catalysis; aza-pinacol rearrangement; indoline; phosphoric acid
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Funding
- 1000 Talents Recruitment Program
- Tsinghua-Peking University Center for Life Science
- National Natural Science Foudation of China [21302107, 21672123, 81671972, 31530082]
- Tsinghua University Research Program [20161080058]
- Grand Challenges Exploration of the Bill and Melinda Gates Foundation [OPP1021992]
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The first catalytic enantioselective asymmetric aza-pinacol rearrangement is reported. The reactions are catalyzed by a chiral phosphoric acid and proceed via a highly organized transition state involving a cyclic aza-ortho-xylylene intermediate to afford the indoline structures with good to excellent enantioselectivity. The synthetic utility of this method is demonstrated by the asymmetric synthesis of a key intermediate to the natural product minfiensine and the identification of a chiral lead compound to repress antibiotic resistance.
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