Journal
ORGANIC LETTERS
Volume 23, Issue 12, Pages 4876-4881Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01600
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Funding
- National Natural Science Foundation of China [21202059]
- China Postdoctoral Science Foundation [2013M541287]
- Jilin Province Science & Technology Development Program [20100538, 20110436, 201215033]
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This study presents an enantioselective domino reaction between 3-vinylindole and p-quinone methide for the preparation of 3-indolyl cyclopenta[b]indoles containing multiple chiral centers. The cascade asymmetric process enabled by chiral imidodiphosphoric acids delivers products with excellent yields, enantioselectivities, and diastereoselectivities.
The development of a stereoselective method for the rapid assembly of structurally complex molecules remains fascinating and challenging in synthetic organic chemistry. Here, we report an enantioselective domino reaction between 3-vinylindole and p-quinone methide for the preparation of 3-indolyl cyclopenta[b]indoles containing multiple chiral centers. Chiral imidodiphosphoric acids enable this cascade asymmetric process, delivering a series of products with excellent yields (<= 99%), enantioselectivities (<= 99%), and diastereoselectivities (<= 20:1 dr).
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