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. 2019 Dec 26;11(8):2175–2180. doi: 10.1039/c9sc05738b

Screening of conditions and promoters for a dienamine-catalyzed asymmetric pyrone Diels–Alder reaction of 22 and 23.

graphic file with name c9sc05738b-u1.jpg
Entry Additive Catalyst Yield (%) dr eec (%)
1a PhCO2Ha 13 52 4.9 : 1 87
2 PhCO2Hb 20 56 5.7 : 1 93
3 Et3Nb 20 13 4.9 : 1 n.d.
4 20 93 6.7 : 1 94
5 13 70 2.3 : 1 90
6 25 64 3.5 : 1 92
7 26 10 3.0 : 1 20
8 27 n.d. n.d.
a

10 mol% loading of both catalyst and benzoic acid.

b

0.1 equiv. added.

c

Measured for major diastereomer.