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Determination of absolute configuration of 1,3‐diols by the modified Mosher's method using their di‐MTPA esters
Author(s) -
Konno Katsuhiro,
Fujishima Toshie,
Liu Zhaopeng,
Takayama Hiroaki
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10035
Subject(s) - chemistry , absolute configuration , chirality (physics) , stereochemistry , diol , absolute (philosophy) , computational chemistry , organic chemistry , philosophy , chiral symmetry breaking , physics , epistemology , quantum mechanics , nambu–jona lasinio model , quark
1,3‐Diols are frequently involved in biologically important compounds and, therefore, determination of the stereochemistry of these structural elements, in particular those in acyclic systems, has been one of the focuses of attention in natural products chemistry. The modified Mosher's method, commonly used for the determination of the absolute configuration of secondary alcohols, was applied to determine the absolute configuration of 1,3‐diols with their di‐MTPA esters. Several epimeric pairs of syn ‐ and anti ‐1,3‐diols with known absolute configurations were converted to the corresponding di‐MTPA esters and the iDelta;δ values were then calculated. For the acyclic syn ‐1,3‐diols, the iDelta;δ values were systematically arranged as predicted from the basic concept of the modified Mosher's method, demonstrating that the method is valid for these compounds. In contrast, the iDelta;δ values were irregularly arranged for the acyclic anti ‐1,3‐diols and, accordingly, this method is not valid for these cases. These results are complementary to those of the previously reported CD exciton chirality method and, hence, the combined use of the modified Mosher's method and the CD exciton chirality method can determine the absolute configuration of the acyclic 1,3‐diols. Also, this method is successfully applicable to cyclic 1,3‐diols irrespective of their relative stereochemistry. Chirality: 14:72–80, 2002. © 2002 Wiley‐Liss, Inc.