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. Author manuscript; available in PMC: 2021 Jul 2.
Published in final edited form as: Org Lett. 2020 Jun 16;22(13):4966–4969. doi: 10.1021/acs.orglett.0c01441

Table 2.

Substrate Scope of the Enantioselective Decarboxylative Allylic Alkylation of Enaminonesa

graphic file with name nihms-1637399-t0005.jpg
entry product R1 R2 yield (%)b ee (%)c
1 2a Me H 95 (93)d 99 (98)d
2 2b Et H 99 98
3 2c CH2OTBS H 96 99
4 2d CH2CH2OTBS H 93 99
5 2e CH2CH2CO2Me H 98 97
6 2f CH2CH2C(O)Me H 90 94
7 2g CH2CH2CN H 99 94
8 2h Bn H 95 96
9 2i p-(OMe)Bn H 99 95
10 2j p-(CF3)Bn H 87 92
11 2k Me Me 92 99
12 2l Me Cl 58 99
a

Conditions: β-ketoester (0.47 mmol), Pd2(dmdba)3 (5.0 mol %), (S)-t-BuPHOX (12.5 mol %), EtOAc (14 mL), 40 °C, 9 h.

b

Isolated yield.

c

Determined by analytical chiral SFC. See Supporting Information for details.

d

Conditions: β-ketoester (12.3 mmol), Pd2(dmdba)3 (0.5 mol %), (S)-t-BuPHOX (1.3 mol %), EtOAc (37 mL), 40 °C.