TY - JOUR
T1 - Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods
AU - Narumi, Fumitaka
AU - Hattori, Tetsutaro
AU - Yamabuki, Waka
AU - Kabuto, Chizuko
AU - Kameyama, Hiroshi
N1 - Funding Information:
The authors are grateful to Emeritus Professor Sotaro Miyano and Professor Nobuyuki Harada of Tohoku University for helpful discussions. F.N. thanks the Asahi Glass Foundation for financial support.
PY - 2005/2/21
Y1 - 2005/2/21
N2 - Inherently chiral anti-O,O′-dibenzyl-p-tert-butylcalix[4]arene 1 was resolved as the (S)-2-methoxy-2-(naphthalen-1-yl)propionic ester by flash chromatography. Conversely, the anti-O,O′-dibutyl analogue 2 was resolved as the (Sa)-2′-methoxy-1,1′-binaphthalene-2-carboxylic ester by crystallization combined with flash chromatography. CD analysis of these compounds indicated the absolute stereochemistries to be (S a)-(+)-1 and (Sa)-(+)-2, respectively, the former of which was confirmed by X-ray crystallographic analysis.
AB - Inherently chiral anti-O,O′-dibenzyl-p-tert-butylcalix[4]arene 1 was resolved as the (S)-2-methoxy-2-(naphthalen-1-yl)propionic ester by flash chromatography. Conversely, the anti-O,O′-dibutyl analogue 2 was resolved as the (Sa)-2′-methoxy-1,1′-binaphthalene-2-carboxylic ester by crystallization combined with flash chromatography. CD analysis of these compounds indicated the absolute stereochemistries to be (S a)-(+)-1 and (Sa)-(+)-2, respectively, the former of which was confirmed by X-ray crystallographic analysis.
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U2 - 10.1016/j.tetasy.2004.11.095
DO - 10.1016/j.tetasy.2004.11.095
M3 - Article
AN - SCOPUS:13844254277
VL - 16
SP - 793
EP - 800
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 4
ER -