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. Author manuscript; available in PMC: 2009 Feb 10.
Published in final edited form as: J Am Chem Soc. 2007 Nov 17;129(49):15398–15404. doi: 10.1021/ja075204v

Table 3.

Asymmetric Allylboration of Benzoyl Iminesa

graphic file with name nihms62971f13.jpg
entry R product % yieldb erc
1 Ph 9a 87 99:1
2 p-CH3-C6H4 9b 83 98:2
3 p-Br-C6H4 9c 86 97.5:2.5
4 p-CH3O-C6H4 9d 85 95:5
5d p-F-C6H4 9e 94 98:2
6d o-F-C6H4 9f 91 95.5:4.5
7d m-CF3-C6H4 9g 89 97.5:2.5
8 2-C4H3O 9h 83 96:4
9 2-C4H3S 9i 81 95:5
10 2-naphthyl 9j 88 96:4
11 (E)-PhCH=CH 9k 82 95.5:4.5
12 PhCH2CH2 9l 83 99.5:0.5
13 c-C6H11 9m 80 98:2
14 t-Bu 9n 81 99.5:0.5
15 BnOCH2 9o 84 96.5:3.5
16 (Z)-EtCH=CH(CH2)2 9p 82 95.5:4.5
a

Reactions were run with 0.5 mmol 4, 0.5 mmol imine, and 15 mol % catalyst and 3Å molecular sieves in toluene for 36 h under Ar, followed by flash chromatography on silica gel.

b

Isolated yield.

c

Determined by chiral HPLC analysis.

d

Reactions were run at 10 °C for 48 h.