TY - JOUR
T1 - Assignment of the relative and absolute configurations of acyclic secondary 1,2-diols
AU - Higashibayashi, Shuhei
AU - Kishi, Yoshito
N1 - Funding Information:
Financial support from the National Institutes of Health (NS 12108) is gratefully acknowledged. S. H. thanks a postdoctoral fellowship from the Naito Foundation.
PY - 2004/12/13
Y1 - 2004/12/13
N2 - The NMR profiles ( 13C-δ, 1H-δ, 1H(OH)-δ, and 3J H,H) of syn- and anti-diols - 3a,b in achiral solvents were found to be very similar to each other. Contrarily, their Δδ (Δδ=δ (R,R)-2-δ (S,S)-2) behaviors in chiral bidentate NMR solvent (R,R)- and (S,S)-BMBA-p-Me (2) were found to be significantly different. On the basis of this NMR characteristic, a method has been developed to predict both the relative and absolute configurations of acyclic secondary 1,2-diols. Both the relative and absolute configurations of acyclic secondary 1,2-diols can be deduced through analysis of the 13C-Δδ (Δδ=δ (R,R)-2-δ (S,S)-2) behaviors of the two alcoholic carbons in chiral bidentate NMR solvent (R,R)- and (S,S)-BMBA-p-Me (2).
AB - The NMR profiles ( 13C-δ, 1H-δ, 1H(OH)-δ, and 3J H,H) of syn- and anti-diols - 3a,b in achiral solvents were found to be very similar to each other. Contrarily, their Δδ (Δδ=δ (R,R)-2-δ (S,S)-2) behaviors in chiral bidentate NMR solvent (R,R)- and (S,S)-BMBA-p-Me (2) were found to be significantly different. On the basis of this NMR characteristic, a method has been developed to predict both the relative and absolute configurations of acyclic secondary 1,2-diols. Both the relative and absolute configurations of acyclic secondary 1,2-diols can be deduced through analysis of the 13C-Δδ (Δδ=δ (R,R)-2-δ (S,S)-2) behaviors of the two alcoholic carbons in chiral bidentate NMR solvent (R,R)- and (S,S)-BMBA-p-Me (2).
KW - Absolute configuration
KW - Chiral NMR solvent
KW - Diols
KW - Relative configuration
UR - http://www.scopus.com/inward/record.url?scp=8444223084&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=8444223084&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2004.08.101
DO - 10.1016/j.tet.2004.08.101
M3 - Article
AN - SCOPUS:8444223084
SN - 0040-4020
VL - 60
SP - 11977
EP - 11982
JO - Tetrahedron
JF - Tetrahedron
IS - 51
ER -