Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 10487-10500Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01516
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Funding
- University of Colorado at Boulder
- NIH [RR026641]
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Chiral 1,2-amino alcohols are privileged scaffolds with important applications as drug candidates and chiral ligands. Although various methods for the preparation of this structural motif have been reported, these methods are limited because of the use of precious metals and ligands. Here, we report a practical and high yielding synthesis of chiral 1,2-amino alcohols using arylglyoxals and pseudoephedrine auxiliary. This reaction is catalyzed by a Bronsted acid and provides morpholinone products in high yields and selectivities. The morpholine ring was converted into 1,2-amino alcohols in a two-step protocol.
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