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. Author manuscript; available in PMC: 2014 Nov 6.
Published in final edited form as: J Am Chem Soc. 2013 Oct 28;135(44):10.1021/ja408561b. doi: 10.1021/ja408561b

Table 2.

Catalytic Asymmetric Synthesis of 1,1-Diarylalkanes from Racemic Benzylic Alcohols: Scope with Respect to the Alcohola

graphic file with name nihms535721u3.jpg
entry benzylic alcohol ee (%) yield (%)b
1 graphic file with name nihms535721t1.jpg R =Me 88 88
2 Et 94 92
3 n-Pr 94 90
4 n-Bu 95 83
5 i-Bu 95 77
6 cyclobutyl 94 51
7c graphic file with name nihms535721t2.jpg 95 80
8 graphic file with name nihms535721t3.jpg 88 90
9 graphic file with name nihms535721t4.jpg 86 59
10d graphic file with name nihms535721t5.jpg 94 77
11 graphic file with name nihms535721t6.jpg 92 84
12 graphic file with name nihms535721t7.jpg 94 84
13 graphic file with name nihms535721t8.jpg 95 88
14 graphic file with name nihms535721t9.jpg 94 75

15 graphic file with name nihms535721t10.jpg X = F 93 87
16 Cl 90 88
17 Br 91 79
18 Ph 92 78
19e graphic file with name nihms535721t11.jpg X = OMe 95 94
20c,e OPiv 84 84

21e graphic file with name nihms535721t12.jpg X = OMe 94 94
22c CF3 89 63
23e graphic file with name nihms535721t13.jpg 92 88

24 graphic file with name nihms535721t14.jpg 81 66
25 graphic file with name nihms535721t15.jpg 91 79
26 graphic file with name nihms535721t16.jpg 93 88
27 graphic file with name nihms535721t17.jpg 83 54
28 graphic file with name nihms535721t18.jpg 94 93
a

All data are the average of two experiments.

b

Yield of purified product.

c

Reaction temperature: −35 °C.

d

Nucleophile: (p-tolyl)ZnI.

e

Nucleophile: PhZnI.