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. Author manuscript; available in PMC: 2010 Mar 25.
Published in final edited form as: Org Lett. 2008 Jun 6;10(13):2705–2708. doi: 10.1021/ol800836v

Table 2.

Ru-catalyzed reductive coupling of aldehydes 3a-3f to 1,1-disubstituted allenes via transfer hydrogenation.a

graphic file with name nihms184659u3.jpg
3a, R = p-NO2Ph 3c, R = 2-(4-NO2-Furyl) 3e, R = CH2OBn
3b, R = p-(CO2Me)Ph 3d, R = o-NO2-Cinnamyl 3f, R = CH2NPhth
entry RCHO, allene product yield % (dr)
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3a, 1a 4a, R1 = Me, R2 = Ph 87% (2:1 dr)
3a, 1b 4b, R1 = Me, R2 = p-FPh 86% (2:1 dr)
3a, 1d 4c, R1 = CH2OMe
R2 = p-MeOPh		 76% (1:1 dr)
3a, 1f 4d, R1 = Me, R2 = CH2Ph 83% (1:1 dr)
3a, 1g 4e, R1 = Et, R2 = n-Bu 82% (1:1 dr)
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3b, 1a 4f 69% (2:1 dr)
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3c, 1a 4g 74% (1:1 dr)
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3d, 1a 4h 61% (2:1 dr)
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3e, 1a 4i, R1= Me, R2 = Ph 71% (1:1 dr)
3e, 1d 4j, R1= CH2OMe
R2 = p-MeOPh		 72% (1:1 dr)
3e, 1g 4k, R1 = Et, R2 = n-Bu 70% (1:1 dr)
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3f, 1a 4l, R1= Me, R2 = Ph 76% (1:1 dr)
3f, 1b 4m, R1 = Me, R2 = p-FPh 77% (1:1 dr)
3f, 1g 4n, R1 = Et, R2 = n-Bu 74% (1:1 dr)
a

Cited yields are of pure isolated material. See Supporting Information for detailed experimental procedures.