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. 2018 Oct 2;8(59):34004–34011. doi: 10.1039/c8ra06814c

% Yield and % ee of (S)-2-[(R)-hydroxy(4-nitrophenyl)methyl] cyclohexan-1-one and (S)-2-[(R)-hydroxy(4-methoxyphenyl)methyl] cyclohexan-1-one.

Entry Catalysts (S)-2-[(R)-hydroxy(4-nitrophenyl)methyl] cyclohexan-1-one (S)-2-[(R)-hydroxy(4-methoxyphenyl)methyl] cyclohexan-1-one
% Yield % ee % Yield % ee
1 No catalysta 67.2 0 1.1 0
2 Prolineb 41.8 73.2 83.0 99.4
3 P1 53.8 22.2 21.5 0
4 CuP1 18.1 87.2 84.7 95.5
5 P2 66.5 22.9 25.8 0
6 CuP2 31.5 88.7 3.3 68.2
7 P3 41.9 94.4 84.4 97.5
8 CuP3 40.2 80.2 29.6 91.0
9 P4c 55.0 98.0 91.2 98.4
10 CuP4 50.5 0 22.1 0
11 P5 56.6 39.6 99.0
12 CuP5 50.7 0 21.2 94.4
a

Negative control.

b

Positive control.

c

P4 was observed to be the best catalyst for both the aldol reactions, followed by P3. The copper-peptides (exceptional for CuP4) catalyzed both the aldol reactions with higher enantioselectivity (94–98%) and yield of products as compared to proline.