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. Author manuscript; available in PMC: 2011 Mar 14.
Published in final edited form as: J Am Chem Soc. 2010 Oct 6;132(39):13600–13603. doi: 10.1021/ja106593m

Table 3.

Asymmetric Aldehyde α-Benzylation: Bromide Scope

graphic file with name nihms266837u5.jpg
entry producta yield, eeb entry producta yield, eeb
1 graphic file with name nihms266837t7.jpg 76% yield
93% ee		 6 graphic file with name nihms266837t8.jpg 90% yielde
82% ee
2 graphic file with name nihms266837t9.jpg 83% yield
90% ee		 7 graphic file with name nihms266837t10.jpg 73% yieldf
90% ee
3 graphic file with name nihms266837t11.jpg 74%yieldc
90% ee		 8 graphic file with name nihms266837t12.jpg 78% yield
87% ee
4 graphic file with name nihms266837t13.jpg 74% yieldd
90% ee		 9 graphic file with name nihms266837t14.jpg 68% yieldg
91% ee
5 graphic file with name nihms266837t15.jpg 75%yielde
91% ee		 10 graphic file with name nihms266837t16.jpg 81% yielde,h
88% ee
a

Stereochemistry assigned by chemical correlation or by analogy.

b

Enantiomeric excess determined by chiral SFC or HPLC.

c

30 mol% organocatalyst used.

d

Performed at 15 °C using Ru(bpy)3Cl2 as the photoredox catalyst; ref 14.

e

Substrate added as the hydrobromic acid salt with an additional equivalent of 2,6-lutidine. The free base organocatalyst was used.

f

Yield determined by 1H NMR.

g

Ir(dF(CF3)ppy)2(dtbbpy)PF6 was employed

as the photoredox catalyst; ref 15.

h

Isolated yield of the corresponding alcohol.