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. Author manuscript; available in PMC: 2016 Sep 9.
Published in final edited form as: J Am Chem Soc. 2015 Aug 27;137(35):11246–11249. doi: 10.1021/jacs.5b07203

Table 3.

Asymmetric Synthesis of Aminoindanesa

graphic file with name nihms797607u3.jpg

entry substrate amine % yieldb er
1
2c
graphic file with name nihms797607t11.jpg graphic file with name nihms797607t12.jpg 98
95
>99:1
99:1
3 4b graphic file with name nihms797607t13.jpg 88 95:5
4 4b graphic file with name nihms797607t14.jpg 90 95:5
5 4b graphic file with name nihms797607t15.jpg 47 89:11
6 4b graphic file with name nihms797607t16.jpg 63 >99:1
7 4b graphic file with name nihms797607t17.jpg 82 97:3
8 graphic file with name nihms797607t18.jpg graphic file with name nihms797607t19.jpg 56 97:3
9 4c graphic file with name nihms797607t20.jpg 59 >99:1
10 graphic file with name nihms797607t21.jpg graphic file with name nihms797607t22.jpg 77 98:2
a

Conditions: Reactions were conducted on a 0.1 mmol scale using 1.0 equiv 4, 1.2 equiv amine, 1.4 equiv LiOtBu, 4 mol % Pd(OAc)2, 10 mol % (S)-tBu-PHOX, toluene (0.1 M), 95 °C, 3–16 h.

b

Isolated yields (average of two or more experiments).

c

The reaction was conducted on a 1.0 mmol scale.