Naturalproductman’s Blog

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CO2 as a protecting group?

Posted by naturalproductman on August 20, 2014

Arjan Kleij and co-workers from ICIQ in Spain have reported in ACIE on the use of carbon dioxide as a protecting group for cis-diols arising from epoxides using an iron or aluminum aminotriphenolate complex to make the carbonate from the epoxide.

carbon dioxide

ACIE paper

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2 Responses to “CO2 as a protecting group?”

  1. milkshake said

    this is quite useful. I remember about 8 years ago I needed to make cis and trans diol in 95%+ ee from a chromene compound which was an excellent substrate for Jacobsen asymmetric epoxidation of styrenes, but a terrible substrate for Sharpless asym dihydroxylation. Trans diol was easy but to get the cis diol from the epoxide, I had to perform double inversion on the benzylic stereocenter (AcBr opening, followed by stoechiometric Ag+ salt). Cyclic carbonate method would have been far nicer.

  2. Reblogged this on ORGANIC CHEMISTRY SELECT.

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