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. Author manuscript; available in PMC: 2023 May 20.
Published in final edited form as: ACS Catal. 2022 May 9;12(10):6172–6179. doi: 10.1021/acscatal.2c01647

Table 1.

Selected optimization experiments in the enantioselective iridium-catalyzed reductive coupling of oxetanone 1a with allyl acetate 2a to form oxetanol 3a.a

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Entry Base (S)-Ligand X Additive 3a (Yield, ee)
1 Cs2CO3 (20 mol%) I CN --- 44%, 98%
2 Cs2CO3 (20 mol%) II CN --- 37%, 98%
3 Cs2CO3 (20 mol%) III CN --- 42%, 99%
4 Cs2CO3 (20 mol%) IV CN --- 44%, 99%
5 Cs2CO3 (20 mol%) V CN --- 40%, 97%
6 Cs2CO3 (20 mol%) VI CN --- 46%, 99%
7 Cs2CO3 (20 mol%) VII CN --- 61%, 99%
8 Cs2CO3 (20 mol%) VII OMe --- 20%, 98%
9 Cs2CO3 (20 mol%) VII NO2 --- 64%, 98%
10 Cs2CO3 (100 mol%) VII NO2 --- 23%, 98%
11 K2CO3 (20 mol%) VII NO2 --- 30%, 99%
12 K2CO3 (100 mol%) VII NO2 --- 79%, 99%
➡13 K2CO3 (100 mol%) VII NO 2 3,4-(NO2)2BzOH 96%, 99%
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a

Yields of material isolated by silica gel chromatography. Enantioselectivities were determined by chiral stationary phase HPLC analysis. See Supporting Information for further details.