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Synfacts 2008(10): 1107-1107  
DOI: 10.1055/s-2008-1078147
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Information from the Solvent

Contributor(s): Benjamin List, Lars Ratjen
S. Garre, E. Parker, B. Ni*, A. D. Headley*
Texas A & M University, Commerce, USA
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

The authors report the concise three-step synthesis of chiral ionic liquids (ILs) 1-3. Their application as chiral solvent in enantioselective Morita-Baylis-Hillman (BH) reactions of aromatic aldehydes and methyl acrylate involving DABCO as Lewis base is accounted. While IL 1 showed only disappointing enantiomeric ratios but good yields, solvent 3 showed significant enantioselectivities (up to 62.5:37.5) and good yields. A mechanistic discussion, elucidating hydrogen bonding of the ionic liquid moiety to the aldehyde is included.