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Chapter 58,723

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Lu, Y.; Hou, C.; Ren, J.; Xin, X.; Xu, H.; Pei, Y.; Dong, H.; Pei, Z.

Molecules 21(5)

2016

ISSN/ISBN: 1420-3049
PMID: 27196888
DOI: 10.3390/molecules21050641
Accession: 058722669
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A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy.

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