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Synfacts 2011(9): 1013-1013
DOI: 10.1055/s-0030-1260922
DOI: 10.1055/s-0030-1260922
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Desymmetrization of meso-Diols via Covalent Substrate Binding Catalysis
X. Sun, A. D. Worthy, K. L. Tan*
Boston College, Chestnut Hill, USA
Further Information
Publication History
Publication Date:
19 August 2011 (online)
Significance
The desymmetrization of meso-diols is a highly useful asymmetric transformation since it can provide synthetically valuable intermediates with theoretically quantitative yields. The authors utilized catalysts 1 as a substrate-binding module as well as a silyl chloride activator. High enantioselectivity was obtained for cyclic and acyclic meso-diols (er up to 97.5:2.5). Also, the substituent adjacent to the imidazole group affects the enantioselectivity dramatically and displays strong match/mismatch effects on the enantioselectivity.