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. Author manuscript; available in PMC: 2012 Dec 7.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Sep 14;50(45):10565–10569. doi: 10.1002/anie.201105536

Table 3.

Conjugate Addition of Acetone Cyanohydrin to 7.a

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Entry 7 R PTC Time (h) Yieldb eec
1d 7a Et CPD-2 24 >95e 86
2d 7a Et CPN-3 24 >95e 78

3 7a Et CPD-2 48 83 95 (S)
4 7a Et CPN-3 24 94 90 (R)

5 7b Me CPD-2 48 79 97 (S)
6 7b Me CPN-3 24 77 92 (R)

7 7c n-C5H11 CPD-2 96 87 96 (S)
8 7c n-C5H11 CPN-3 24 84 92 (R)

9 7d iPr CPD-2 48 83 95 (S)
10 7d iPr CPN-3 24 71 91 (R)

11 7e CH2iPr CPD-2 96 78 98 (S)
12 7e CH2iPr CPN-3 24 80 94 (R)

13 7f CH2CH2Ph CPD-2 96 75 95 (S)
14 7f CH2CH2Ph CPN-3 24 70 93 (R)
a

Unless noted reactions were performed with 0.1 mmol of 7 and 0.2 mmol acetone cyanohydrin, 0.12 mmol Rb2CO3 in 1 mL of Toluene/CHCl3 (7:3 v/v) with 10 mol% CPD-2(or 10 mol% CPN-3a).

b

Isolated yield.

c

Determined by chiral HPLC. The Absolute configuration is reported in parenthesis, see supporting information for details.

d

0.12 mmol Cs2CO3 used instead of Rb2CO3