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. 2018 Oct 5;57(44):14593–14596. doi: 10.1002/anie.201808919

Table 1.

Photocycloaddition reaction of phenanthrene‐9‐carboxaldehyde (1 a) and 2,3‐dimethyl‐2‐butene in the presence of chiral Lewis acids 3. Inline graphic

Entry[a] λ [a]
[nm]
Lewis
acid[b]
Loading
[mol %]
t [a]
[h]
Yield[c]
[%]
ee [d]
[%]
1 424 3 a 50 14 53 56
2 435 3 a 50 9 43 70
3 457 3 a 50 11 49 79
4 457 3 b 50 11 54 84
5 457 3 c 50 11 62 97
6 457 3 c 25 19 79 94
7 457 3 c 10 26 81 94

[a] The reaction was performed at −78 °C with a substrate concentration of c=20 mm in CH2Cl2 at the indicated wavelength (λ) and for the indicated period of time (t). The olefin was used in excess (30 equiv). [b] 3 a: Ar=2,4,6‐trifluorophenyl; 3 b: Ar=2‐(trifluoromethyl)phenyl; 3 c: Ar=2,6‐dimethylphenyl. [c] Yield of isolated product. [d] The enantiomeric excess (ee) was determined by chiral‐phase HPLC analysis.