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. 2021 Jun 16;23(13):4986–4990. doi: 10.1021/acs.orglett.1c01403

Table 1. Effect of the Variation of the Aziridine and Allyl Reagent.

graphic file with name ol1c01403_0009.jpg

entry R reagent product yield (%)
1a,b CO2tBu allyl acetate 12a 87
2b,c COMe allyl acetate 12b 56d
3b,c CONHEt allyl acetate 12c 60d
4a,b CN allyl acetate 12d 0e
5d CO2tBu none 13a 83
6a COMe none 13b 82
7a CONHEt none 13c 44
8a CN none 13d 0e
9a,f CO2tBu none 13a 0
10a,g CO2tBu none 13a 0
a

Reaction performed at 70 °C.

b

Performed in the presence of 1.3 equiv of K2CO3.

c

Reaction performed at 30 °C.

d

Yield determined by 1H NMR using 1,3,5-trimethoxybenzene as the internal standard.

e

Slow conversion to retro-ene product 3 was observed.9

f

Performed using Pd(PPh3)4.

g

Performed using Pd2(dba)3/PPh3.