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. Author manuscript; available in PMC: 2011 Aug 11.
Published in final edited form as: J Am Chem Soc. 2010 Aug 11;132(31):10630–10633. doi: 10.1021/ja104777u

Table 2.

NHC–Cu-Catalyzed Enantioselective Boronate Conjugate Additions to Aryl-Substituted α,β-Unsaturated Estersa

graphic file with name nihms-223491-f0007.jpg
entry aryl R time (h) conv (%)b yield (%)c erd
1 Ph Me 24 >98 80 96.5:3.5
2 o-BrC6H4 Me 24 >98 92 95.5:4.5
3 o-MeC6H4 Me 24 38 31 53:47
4 2-naphthyl Me 36 >98 >98 96.5:3.5
5 m-BrC6H4 Me 18 >98 96 97:3
6 p-BrC6H4 Me 12 >98 93 98:2
7 p-CF3C6H4 Me 24 >98 93 99:1
8 p-OMeC6H4 Me 36 73 69 95:5
9 Ph Et 18e >98 90 94.5:5.5
a

See Table 1.

b

See Table 1.

c

Yields of purified products.

d

Determined by HPLC analysis. See the Supporting Information for details.

e

Performed at –15 °C.