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Title

A two-step chemical/chiroptical method for determining absolute configurations of α-hydroxy acids

Authors
Rickman, Barry H.
Nakanishi, Koji
Berova, Nina
Published in Tetrahedron. 1998, vol. 54, no. 20, p. 5041-5064
Abstract A general, chemical/chiroptical approach based on the CD exciton chirality method has been developed to determine the absolute configuration of α-hydroxy acids. This approach consists of amidation of the carboxyl group with ethanolamine followed by derivatization with the hydrophobic 10,15,20-triphenylporphyrinyl-5-benzoyl chromophore to form p,p-bisporphyrin derivatives which undergo intramolecular stacking. The sign of the observed bisignate couplet resulting from this stacking (in methylcyclohexane) is dictated by the preferred lower energy conformer and reflects the absolute configuration of the stereogenic center.
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RICKMAN, Barry H. et al. A two-step chemical/chiroptical method for determining absolute configurations of α-hydroxy acids. In: Tetrahedron, 1998, vol. 54, n° 20, p. 5041-5064. https://archive-ouverte.unige.ch/unige:6971

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Deposited on : 2010-06-18

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