A cautionary note on the use of commercial (R)-MTPA-Cl and (S)-MTPA-Cl in determination of absolute configuration by Mosher ester analysis

Joshi, B. S. ; Pelletier, S. W. (1999) A cautionary note on the use of commercial (R)-MTPA-Cl and (S)-MTPA-Cl in determination of absolute configuration by Mosher ester analysis Heterocycles, 51 (1). pp. 183-184. ISSN 0385-5414

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Official URL: http://sciencelinks.jp/j-east/article/199909/00001...

Abstract

While the absolute configuration of a Mosher ester derivative (MTPAOR) is identical with that of the Mosher acid (MTPAOH) precursor, it is opposite that of the Mosher acid chloride (MTPA-Cl). Since (R)-MTPA-Cl and (S)-MTPA-Cl are now commercially available, incorrect conclusions may be drawn in deriving the absolute configuration, if this fact is overlooked. The absolute configuration of (−)-vasicinone (1) derived by Mosher ester analysis has been revised as 3S. Mosher ester analysis of (−)-vasicine (2) confirmed a 3S configuration for this alkloid.

Item Type:Article
Source:Copyright of this article belongs to Japan Institute of Heterocyclic Chemistry.
ID Code:86863
Deposited On:13 Mar 2012 15:03
Last Modified:13 Mar 2012 15:03

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