Journal
ORGANIC LETTERS
Volume 21, Issue 8, Pages 2795-2799Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00757
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Funding
- NSFC [21672145, 21602131, 51733007]
- Shanghai Education Development Foundation [16SG10]
- Shanghai Municipal Education Commission [16SG10]
- Science and Technology Commission of Shanghai Municipality [17JC1403700]
- Drug Innovation Major Project of the Ministry of Science and Technology of China [2018ZX09711001-005-002]
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A method of SPINOL-derived chiral phosphoric acid catalyzed asymmetric intermolecular N-hydroxyalkylation of multisubstituted indoles with ethyl glyoxalates is described in this report. This protocol provides an alternative, convenient, and direct strategy for efficient access to structurally unique alpha-chiral indole N,O-acyclic aminals with a broad substrate scope and good to excellent enantioselectivities. The synthetic utility of this methodology is illustrated by a gram-scale experiment and the subsequent efficient synthesis of more complex chiral N,O-aminal indole derivatives.
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