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. Author manuscript; available in PMC: 2020 Jan 4.
Published in final edited form as: ACS Catal. 2018 Nov 20;9(1):242–252. doi: 10.1021/acscatal.8b04132

Table 4.

Carbamate substrate scope.a

graphic file with name nihms-1007693-t0015.jpg
entry R1 R2 time (h) yield (%)b erc
1 H C6H5 (c) 24 99 94:6
2 H 4-OMeC6H4 (d) 24 99 93:7
3 H 4-CF3C6H4 (e) 24 98 93:7
4 H 4-BrC6H4 (f) 24 94 94:6
5 H graphic file with name nihms-1007693-t0016.jpg 24 95 92:8
6 H 4-f-BuC6H4 (h) 24 97 94:6
7 H graphic file with name nihms-1007693-t0017.jpg 24 96 93:7
8 H CH3CH2 (j) 84 96 85:15
9 H C6H5CH2 (k) 72 95 82:18
10 CH3 C6H5 (l) 72 94 80:20
a

Reaction conditions: Cyclobutanone 4 (0.10 mmol, 1.0 equiv), P41 (2.5 mol%), and H2O2 (30% w/w aq. 1.5 equiv) at −15 °C with [4c] = 0.05 M CHCl3. Reported results are the average of two trials.

b

Isolated yield after chromatography.

c

Enantiomeric ratios were determined by CSP-HPLC analysis.

See supporting information for details on assignment of absolute configuration. The configuration of products 5c-d, 5g–l were assigned in analogy to 5e and 5f.