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. Author manuscript; available in PMC: 2017 Sep 21.
Published in final edited form as: J Am Chem Soc. 2016 Sep 12;138(37):12069–12072. doi: 10.1021/jacs.6b08486

Table 3.

Phosphine-Catalyzed Asymmetric Synthesis of Benzylic Ethers: Scope with Respect to the Alcohola

graphic file with name nihms819660u5.jpg
entry H–OR ee (%) yield (%)b
1 graphic file with name nihms819660t8.jpg 95 90
2 94 88
3c 91 86
4 graphic file with name nihms819660t9.jpg 94 88
5 graphic file with name nihms819660t10.jpg 91 86
6c graphic file with name nihms819660t11.jpg 93 74
7d HOMe 92 88
8 graphic file with name nihms819660t12.jpg 96 82
9 graphic file with name nihms819660t13.jpg 96 (95e) 64 (79e)
10 graphic file with name nihms819660t14.jpg 96 75
a

All data are the average of two experiments.

b

Yield of purified, isolated product.

c

Amount of nucleophile: 2.0 equiv.

d

The methyl, rather than the t-butyl, ester of the alkynoate was used.

e

Catalyst loading: 20% (S)–1.