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. Author manuscript; available in PMC: 2014 Oct 11.
Published in final edited form as: Adv Synth Catal. 2013 Oct 7;355(14-15):3037–3057. doi: 10.1002/adsc.201300640

Table 2.

Scope of the Catalytic, Asymmetric Borylation of α,β-Unsaturated Amides with BBA.

graphic file with name nihms569059u2.jpg
entry product[a]
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2a 90%, 93:7 er (85%, 93:7 er)[b]
2 graphic file with name nihms569059t2.jpg
2b 82%, 97:3 er
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2c 80%, 92:8 er
4 graphic file with name nihms569059t4.jpg
2d 82%, 95:5 er (71%, 1.5 equiv BBA)[c]
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2e 51%, 93:7 er
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2f 86%, 98:2 er
7 graphic file with name nihms569059t7.jpg
2g 82%, 92:8 er
8 graphic file with name nihms569059t8.jpg
2h 84%, 97:3 er
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2i 92%, 96:4 er
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2j 71%, 76:24 er
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2k 86%, 70:30 er
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2l 80%, 66:34 er
13 graphic file with name nihms569059t13.jpg
2m 77%, 72:28 er
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2n 85%, 78:22 er
[a]

Enantiomeric excess was determined by oxidation of 2 followed by SFC analysis of the corresponding alcohol.

[b]

Reaction performed on a 5.5 mmol scale with 2.5 mol % Cu(MeCN)4PF6, 2.5 mol % L2.

[c]

Reaction performed on a 3 mmol scale.