Diastereoselective sp(2)-sp(3) coupling of sugar enol ethers with unactivated cycloalkenes: new entries to C-branched sugars.

Abstract

Sugar enol ethers undergo efficient coupling at C-2 with unactivated cycloalkenes under a low Pd loading affording allylic substitution products. High diastereoselectivity was observed at the allylic centre with sterically hindered substrates. Generation of a π-allyl complex by the Pd(ii) catalyst via cleavage of the allylic C-H bond of the cycloalkene may be responsible for the formation of sp(2)-sp(3) coupling products.

Cite this paper

@article{Hussain2016DiastereoselectiveSC, title={Diastereoselective sp(2)-sp(3) coupling of sugar enol ethers with unactivated cycloalkenes: new entries to C-branched sugars.}, author={Nazar Hussain and Madhu Babu Tatina and Faheem Rasool and Debaraj Mukherjee}, journal={Organic & biomolecular chemistry}, year={2016}, volume={14 42}, pages={9989-9992} }