Journal
ORGANIC LETTERS
Volume 11, Issue 11, Pages 2249-2252Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900538q
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- Welch Foundation [AX-1593]
- National Institute of General Medical Sciences [1SC1GM082718-01A1]
- NIH [G12 RR013646]
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beta-(3-Hydroxypyrazol-1-yl) ketones have been prepared in high yields and excellent enantioselectivities (94-98% ee) via a Michael addition reaction between 2-pyrazolin-5-ones and aliphatic acyclic alpha,beta-unsaturated ketones using 9-epi-9-amino-9-deoxyquinine as the catalyst. These results account for the first example of an aza-Michael addition of the ambident 2-pyrazolin-5-one anion to a Michael acceptor.
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