Skip to main content
. Author manuscript; available in PMC: 2011 Sep 8.
Published in final edited form as: J Am Chem Soc. 2010 Sep 8;132(35):12216–12217. doi: 10.1021/ja105772z

Table 1.

CDR of 2 at −45 °C for 3 h using ligand 8 (or 9 where noted).

graphic file with name nihms228436u2.jpg
Entry E+ Product(s) % Yield er
1 Me3SiCl (S)-3 74 96:4
2 Bu3SnCl (S)-10 66 96:4
3 Bu3SnCl (R)-10 62 97:3a
4 CO2 (R)-11 78 98:2
5 MeOCOCl (R)-12 88 >99:1
6 MeOCOCl (S)-12 85 >99:1a
7 PhNCO (R)-13 68 >99:1
8 Allyl bromide (R)-14 63 95:5b
9 Allyl bromide (S)-14 59 96:4a,b
10 BnBr (R)-15 65 >99:1b
11 Cyclohexanone graphic file with name nihms228436t1.jpg
(R)-16
60 94:6
12 PhCHOc graphic file with name nihms228436t2.jpg
17
74 (62:38 dr) >99:1 & 98:2
13 1-NpCHOc graphic file with name nihms228436t3.jpg
18
66 (82:18 dr) 94:6 & 93:7
14 CH3CHOc graphic file with name nihms228436t4.jpg
19
78 (85:15 dr) >99:1 for both
a

Using ligand 9

b

via Negishi cross coupling

c

Major diastereomer illustrated