A general thermolabile protecting group strategy for organocatalytic metal-organic frameworks

J Am Chem Soc. 2011 Apr 20;133(15):5806-9. doi: 10.1021/ja202223d. Epub 2011 Mar 28.


We present a general strategy for incorporating organocatalytic moieties into metal-organic frameworks (MOFs). The organocatalytic units are protected by a thermolabile protecting group during MOF synthesis and then unveiled by a simple postsynthetic heating step. The strategy is exemplified using a thermolabile tert-butoxycarbonyl (Boc) protecting group for a proline moiety, the removal of which endows the resulting cubic zinc(II) IRMOF with catalytic activity for asymmetric aldol reactions. The bulky Boc groups also prevent framework interpenetration, producing open MOFs that can admit relatively large substrates.