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. Author manuscript; available in PMC: 2013 Jan 6.
Published in final edited form as: Org Lett. 2011 Dec 19;14(1):422–425. doi: 10.1021/ol203242r

Table 2.

Representative PQS-proline (2)-Catalyzed Reactionsa

graphic file with name nihms345448u3.jpg
entry product time (h) yieldb (%) ant i:sync eed (%)
1 graphic file with name nihms345448t4.jpg
9a
30 88 82:18 90
2 graphic file with name nihms345448t5.jpg
9b
18 90 90:10 90
3 graphic file with name nihms345448t6.jpg
9c
48 74 86:14 92
4 graphic file with name nihms345448t7.jpg
9d
36 80 83:17 91
5 graphic file with name nihms345448t8.jpg
9e
18 85 85:15 79
6 graphic file with name nihms345448t9.jpg
9f
30 80 90:10 97
7 graphic file with name nihms345448t10.jpg
9g
36 82 68:32 86
8 graphic file with name nihms345448t11.jpg
9h
18 85 89:11 75
9 graphic file with name nihms345448t12.jpg
9i
36 82 84:16 86
10 graphic file with name nihms345448t13.jpg
9j
24 90 90:10 91
a

The reactions were performed with aldehyde (0.1 mmol), ketone (0.5 mmol) and catalyst 2 (0.01 mmol) at rt.

b

Combined yield of isolated diastereomers.

c

Determined by 1H NMR of the crude product.

d

Determined by chiral-phase HPLC analysis for anti-product.