TY - JOUR
T1 - Efficient 1H NMR chiral discrimination of sulfoxides caused by the dynamic nature of (R,R)-3′,3″-biBINOL
AU - Kawanami, Toshio
AU - Ishizuka, Kentaro
AU - Furuno, Hiroshi
AU - Shiota, Yoshihito
AU - Yoshizawa, Kazunari
AU - Inanaga, Junji
N1 - Funding Information:
This work was supported by JSPS KAKENHI (Grant-in-Aid for Scientific Research) Grant Numbers 17065017 , 23350021 , and 23750176 , and also by the “Joint Project of Chemical Synthesis Core Research Institutions”. The grant for young researchers of the Kyushu University Global COE Program “Science for Future Molecular Systems” (to H.F.) and Sasagawa Scientific Research Grant from The Japan Science Society (to T.K.) are also acknowledged.
Publisher Copyright:
© 2017 Elsevier Ltd
PY - 2017/11/15
Y1 - 2017/11/15
N2 - A chiral BINOL dimer, (R,R)-3′,3″-BiBINOL, which possesses both rigid (atropos) and dynamic (tropos) axial chiralities, was found to work as an effective NMR chiral solvating reagent for the determination of the enantiomeric purities of various chiral sulfoxides. The unique chiral discrimination mechanism was also revealed by using DFT calculations and X-ray crystallographic analysis.
AB - A chiral BINOL dimer, (R,R)-3′,3″-BiBINOL, which possesses both rigid (atropos) and dynamic (tropos) axial chiralities, was found to work as an effective NMR chiral solvating reagent for the determination of the enantiomeric purities of various chiral sulfoxides. The unique chiral discrimination mechanism was also revealed by using DFT calculations and X-ray crystallographic analysis.
UR - http://www.scopus.com/inward/record.url?scp=85032890513&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85032890513&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2017.10.008
DO - 10.1016/j.tetasy.2017.10.008
M3 - Article
AN - SCOPUS:85032890513
SN - 0957-4166
VL - 28
SP - 1587
EP - 1590
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 11
ER -