Design and synthesis of bistereogenic chiral ionic liquids and their use as solvents for asymmetric Baylis–Hillman reactions

Abstract

Three novel chiral ionic liquids (CILs) containing two chiral centers in the side chain bonded to the 2-position of the imidazolium cation and different anions have been synthesized, characterized and used as chiral solvents for asymmetric Baylis-Hillman (BH) reactions; good yields and fair enantioselectivities were obtained.

Chiral anion-triggered helical poly(ionic liquids)

“…The solvent was rotoevaporated and crude was purified by column chromatography (hexane/ethyl acetate 85/15) to provide the desired products. 81,82 Spectral details for synthesized compounds. All spectral data of the synthesized compounds were matching with literature reports (see supporting information for 1 H, 13 C, GC-MS, specific rotation measurements, HPLC, DSC and TGA spectral data).…”

Catalytic Asymmetric Baylis–Hillman Reactions and Surroundings

“…Recently, the groups of both Ni and Headly [86] designed a new chiral IL (120) by incorporating chiral side chains on the C-2 position of the imidazolium cation ring. This IL was adopted as a reaction medium for reactions between aldehydes and acrylates in the presence of DABCO, and the corresponding adducts were obtained in good yields and 2-24% ee (Scheme 10.73).…”

Aggregation behaviour of chiral ionic liquids

“…They have been successfully used in analytical applications such as stationary phases in gas chromatography, 1,2 or as electrolytes in capillary electrophoresis, [3][4][5][6] as well as in asymmetric synthesis. Prominent examples are the Diels-Alder reaction, 7-9 the Baylis-Hillman reaction, [10][11][12] Michael additions, 13 and asymmetric hydrogenations. [14][15][16] CILs have also been used as effective organocatalysts.…”