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. Author manuscript; available in PMC: 2013 Jun 6.
Published in final edited form as: J Am Chem Soc. 2012 May 29;134(22):9090–9093. doi: 10.1021/ja303116v

Table 2.

Scope of Aldehyde in Enantioselective Vinylationa,b,c

graphic file with name nihms381514u2.jpg
1 graphic file with name nihms381514t1.jpg 82% yield 94% ee 2d,e graphic file with name nihms381514t2.jpg 83% yield 96% ee
3 graphic file with name nihms381514t3.jpg 75% yield 99% ee 4 graphic file with name nihms381514t4.jpg 79% yield 99% ee
5 graphic file with name nihms381514t5.jpg 81% yield 91% ee 6 graphic file with name nihms381514t6.jpg 73% yield 96% ee
7 graphic file with name nihms381514t7.jpg 84% yield ≥20:1 dr 8f graphic file with name nihms381514t8.jpg 81% yield ≥20:1 dr
a

Absolute configuration assigned by chemical correlation or analogy.

b

Isolated yield of the corresponding alcohol.

c

Enantiomeric excesss determined by chiral HPLC analysis of the corresponding alcohol.

d

Using 20 mol% 3.

e

Using 20 mol% CuBr.

f

Using (S,S)-3 catalyst.