Optically Active Polymers with Chiral Recognition Ability

Yashima, Eiji; Yamamoto, Chiyo

doi:10.1002/chin.200411256

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chiral discrimination of a chiral host to a racemic guest, which plays an important role for the separation of enantiomers and the resolution of chiral drugs, is an important part of molecular recognition. [1][2][3] The inclusion resolution method, which is established based on the chiral host stereoselectively interacting with one enantiomer of the racemic guests via intermolecular forces such as π-π interactions, hydrogen bonding, and Van der Waals' force, has been developed as an important chiral resolution method in the past two decades. [4][5][6][7] However, simultaneous complexation of a chiral host to two enantiomers of a racemic guest is seldom observed, although heterorecognition of an achiral host to a racemic guest has been reported.…”

Section: Introductionmentioning

confidence: 99%

Effects of solvent on inclusion complexation of a chiral dipeptide toward racemic BINOL

Yang

Shi

et al. 2016

Chirality

View full text Add to dashboard Cite

The effects of reaction solvent on inclusion complexation of a chiral dipeptide (3S,6S)-1 derived from (S)-proline toward racemic BINOL was investigated, discovering that the reaction solvent played a crucial role in determining the inclusion complexation behavior of dipeptide (3S,6S)-1 toward rac-BINOL. (3S,6S)-1 did not show any chiroselective or achiroselective complexation toward rac-BINOL in polar protic solvents such as methanol and ethanol, polar aprotic solvents including trichloromethane and THF, while in polar aprotic solvent ethyl acetate and apolar aprotic solvents benzene, (3S,6S)-1 displayed achiroselective complexation toward rac-BINOL. However, the resulting heterocomplex HC-2 from benzene and HC-3 from ethyl acetate have a different composition. Single crystal X-ray diffraction analysis demonstrates that the two heterocomplexes are formed via different H-bond interaction patterns, in which the reaction solvent has a dramatic effect. Furthermore, this work provides a relatively green method for quantitative enantiomeric enrichment of nonracemic BINOL, in which unacceptable and toxic benzene was replaced by ethyl acetate.

show abstract