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. Author manuscript; available in PMC: 2012 Aug 10.
Published in final edited form as: J Am Chem Soc. 2011 Jul 15;133(31):11936–11939. doi: 10.1021/ja205107x

Table 3.

Enantioselective Alkylation: Carboxylic Acid Scopea

1 2 3 4 5 6 7 8
graphic file with name nihms-377939-t0015.jpg
96% ee
84% yield
graphic file with name nihms-377939-t0016.jpg
96% ee
81% yield
graphic file with name nihms-377939-t0017.jpg
93% ee
65% yield
graphic file with name nihms-377939-t0018.jpg
89% ee
71% yield
graphic file with name nihms-377939-t0019.jpg
96% ee
83% yield
graphic file with name nihms-377939-t0020.jpg
93% ee
82% yield
graphic file with name nihms-377939-t0021.jpg
94% ee
82% yield
graphic file with name nihms-377939-t0022.jpg
93% ee
87% yield
9 10 11 12 13 14 15 16
graphic file with name nihms-377939-t0023.jpg
92% ee
82% yield
graphic file with name nihms-377939-t0024.jpg
92% ee
89% yield
graphic file with name nihms-377939-t0025.jpg
96% ee
88% yield
graphic file with name nihms-377939-t0026.jpg
97% ee
60% yield
graphic file with name nihms-377939-t0027.jpg
92% ee
62% yield
graphic file with name nihms-377939-t0028.jpg
90% ee
85% yield
graphic file with name nihms-377939-t0029.jpg
0% ee
12% yield
graphic file with name nihms-377939-t0030.jpg
95% ee
61% yieldb
17 18 19 20 21 22 23 24
graphic file with name nihms-377939-t0031.jpg
84% ee
71% yield
graphic file with name nihms-377939-t0032.jpg
X=H, 91% ee,
87%
X=F, 85% ee,
73%
graphic file with name nihms-377939-t0033.jpg
92% ee
87% yield
graphic file with name nihms-377939-t0034.jpg
88% ee
87% yield
graphic file with name nihms-377939-t0035.jpg
94% ee
96% yield
graphic file with name nihms-377939-t0036.jpg
97% ee
78% yield
graphic file with name nihms-377939-t0037.jpg
91% ee
70% yield
graphic file with name nihms-377939-t0038.jpg
96% ee
89% yield
a

Enantiomeric excess was determined by HPLC using a chiral stationary phase (see the Supporting Information for details).

b

Isolated yield of the corresponding alcohol over two steps after reduction of the acid with LiAlH4.