Dynamic molecular propeller: Supramolecular chirality sensing by enhanced chiroptical response through the transmission of point chirality to mobile helicity

Journal of the American Chemical Society

Volumn 131, Issue 46, 2009, Pages 16896-16904

  Katoono, Ryo ^a,b   Kawai, Hidetoshi ^a,c   Fujiwara, Kenshu ^a   Suzuki, Takanori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL AUXILIARIES; CHIRAL RECOGNITION; CONFORMATIONAL CHANGE; DITOPIC GUESTS; HELICITIES; PHENYLEPHRINE; SUPRAMOLECULAR CHIRALITY; SUZUKI-MIYAURA COUPLING; TEREPHTHALAMIDES; THROUGH TRANSMISSION;

CHIRALITY; DYNAMIC RESPONSE; STEREOCHEMISTRY; WIRELESS NETWORKS;

ENANTIOMERS;

AMMONIUM DERIVATIVE; BROMINE DERIVATIVE; HELICASE; NITROGEN; PHENYLEPHRINE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; MOLECULAR DYNAMICS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; SUZUKI REACTION;

EID: 70450164018     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906810b     Document Type: Article

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46. 23 where the matched pair of syn-(R,R)-1b-Me and (S,S)-3 gave strong chiroptical output from the cooperative preference for (M)-helicity, as expected. Mismatched enantiomeric guest (R,R)-3 had much smaller effects on the CD spectrum. The monotopic guest (R)-5 failed to modify the CD spectrum, as in the combination of syn-1a-Me and (R)-5.
47. As shown by the lack of induction of a Cotton effect upon the mixing of conformationally stable anti-1a-Me and chiral guest (R,R)-3, the chiral amide anti-1b-Me does not act as a host for the ditopic guests (R,R)/(S,S)-3.