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. Author manuscript; available in PMC: 2010 Apr 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2008;47(28):5220–5223. doi: 10.1002/anie.200801359

Table 1.

Carbonyl propargylation from the alcohol oxidation level by ruthenium-catalyzed transfer hydrogenation.a

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2a, R =p-NO2Ph 2f, R =p-BrPh 2k, R =geranyl
2b, R =phenyl 2g, R =2-furyl 2l, R =crotyl
2c, R =p-MeOPh 2h, R =3-indolyl 2m, R =cyclopropyl
2d, R =o-MeOPh 2i, R =2-(6-BrPy) 2n, R =benzyl
2e, R =5-piperonyl 2j, R =cinnamyl 2o, R =n-pentyl
Coupling to benzylic alcohols
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3a 3b 3c
65% yield 81% yield 81% yield
1:1 d.r. 1:1 d.r. 1:1 d.r.
graphic file with name nihms195850t4.jpg graphic file with name nihms195850t5.jpg graphic file with name nihms195850t6.jpg
3d 3e 3f
91% yield 83% yield 73% yield
2:1 d.r. 2:1 d.r. 1:1 d.r.
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3g 3h 3i
71% yield 94% yield 42% yield
1.5:1 d.r. 1:1 d.r. 1.3:1 d.r.
Coupling to allylic alcohols
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3j 3k 3l
68% yield 63% yield 72% yield
1:1 d.r. 1.5:1 d.r. 2:1 d.r.
Coupling to aliphatic alcohols
graphic file with name nihms195850t13.jpg graphic file with name nihms195850t14.jpg graphic file with name nihms195850t15.jpg
3m 3n 3o
75% yield 70% yield 72% yield
2:1 d.r. 1:1 d.r. 2:1 d.r.
a

Yields of isolated material. Standard reaction conditions employed 1 equivalent of alcohol/aldehyde and 2 equivalents of enyne. See the Supporting Information for detailed experimental procedures. Py =pyridine.