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. Author manuscript; available in PMC: 2012 Sep 21.
Published in final edited form as: J Am Chem Soc. 2011 Aug 25;133(37):14578–14581. doi: 10.1021/ja206997e

Table 2.

Substrate scope

graphic file with name nihms320429u2.jpg
entry substrate product time (h) yield (%)a ee (%)b
1c,d graphic file with name nihms320429t1.jpg
5c
graphic file with name nihms320429t2.jpg
6
48 74 91
2 11
R=Me
R′=H
12 72 70 90
3 13
R=H
R′=Me
14 72 66 89
4 15
R=Me
R′=Me
16 96 51 89
5 17
R=H
R′=Ph
18 72 48 86
6 19
R=CO2Et
R′=H
20 72 66 90
7e 21
R=CO2Me
R′=Me
22 96 37 80
8c,d graphic file with name nihms320429t3.jpg
23
graphic file with name nihms320429t4.jpg
24
72 54 95
9 graphic file with name nihms320429t5.jpg
25
graphic file with name nihms320429t6.jpg
26
72 42 88
10d graphic file with name nihms320429t7.jpg
27
graphic file with name nihms320429t8.jpg
28
72 77 90
11 graphic file with name nihms320429t9.jpg
29
graphic file with name nihms320429t10.jpg
30
72 70f 89f
a

Isolated yields after chromatography on silica gel.

b

Determined by HPLC using commercial chiral columns.

c

10 mol% 10 + 8.

d

The absolute stereochemistry of 24 and derivatives of 28 and 6 were determined by Xray crystallography and that of all other products was assigned by analogy.

e

20 mol% 10 + 8.

f

Determined on the free alcohol.