Allenylboronic Acid Pinacol Ester

Aldrich ChemFiles 2007, 7.1, 6.

Aldrich ChemFiles 2007, 7.1, 6.

The allenylboronate platform has recently been demonstrated to undergo multicomponent reactions in a completely regio- and stereoselective fashion.1 Yoshida and co-workers successfully utilized this three-carbon building block in a concise synthesis of rolipram, which is a selective inhibitor of phosphodiesterase-4 (PDE-4), an anti-inflammatory agent and antidepressant.1b In the course of the fourcomponent reaction both a C–C and C–N bond are formed, presumably through a Pd-allyl intermediate.


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Materials

     

References

  1. a) Tonogaki, K. et al. Org. Lett. 2006, 8, 1419. (b) Tonogaki, K. et al. J. Am. Chem. Soc. 2006, 128, 1464. (c) Bustelo, E. et al. J. Am. Chem. Soc. 2005, 127, 11582.

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