Synfacts 2009(12): 1409-1409  
DOI: 10.1055/s-0029-1218195
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Mukaiyama Aldol Reaction Catalyzed by a MOF-Based Fe³+ Complex

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
K. K. Tanabe, S. M. Cohen*
University of California, San Diego, USA
Engineering a Metal-Organic Framework Catalyst by Using Postsynthetic Modification
Angew. Chem. Int. Ed.  2009,  48:  7424-7427  
Further Information

Publication History

Publication Date:
20 November 2009 (online)


A metal-organic framework (MOF) based Fe³+ catalyst was developed and applied to the Mukaiyama aldol reaction. Thus, the MOF-based Fe³+, UMCM-1-AMFesal, was prepared by condensation of MOF composite UMCM-1-NH2 with acid anhydride 1 followed by metalation with Fe(acac)3. The Mukaiyama aldol reaction of aldehydes 5a,b and a silyl ketene acetal 6 was carried out with UMCM-1-AMFesal (0.1 mol% Fe) to give the corresponding β-hydroxy esters in 7011% yield (7a) and 5318% yield (7b). The catalyst was reused twice without loss of catalytic activity.


The preparation of UMCM-1-NH2 (University of Michigan Crystalline Material-1-NH2), consisting of 4,4′,4′′-benzene-1,3,5-triyl-tribenzoate (3), 2-amino-1,4-benzenedicarboxylic acid (4), and Zn(NO3)2, was previously reported (Inorg. Chem. 2009, 48, 296). UMCM-1 was originally prepared by Matzger and co-workers ­(Angew. Chem. Int. Ed. 2008, 4, 677).