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. Author manuscript; available in PMC: 2009 Jul 23.
Published in final edited form as: J Am Chem Soc. 2008 Jun 25;130(29):9214–9215. doi: 10.1021/ja803094u

Table 4.

Diels-Alder Reactions of Electron-rich 2′-Hydroxychalcones

graphic file with name nihms-83440-t0016.jpg
entry 2′-hydroxychalcone product conditiona Yield(%)b
1 27: R1=OMe, R2,R3,R4=H 28 A
B
68
36
2 29: R1=OAc, R2,R3,R4=H 30 A
B
84
55
3 31: R1,R2=OMe, R3,R4=H 32 A 33
4 33: R1,R2=OAc, R3,R4=H 34 A 72
5 35: R1,R3,R4=OMe, R2=H 36 A 18
6 37: R1,R3,R4=OAc, R2=H 38 A 61
a

Condition A: 20/40/120/20 mol% CoI2/8/ZnI2/Bu4NBH4; condition B: 120/20 mol% ZnI2/Bu4NBH4, see Supporting Information.

b

Isolated yields.