Journal ArticleDOI
New chiral anisotropic reagents, NMR tools to elucidate the absolute configurations of long-chain organic compounds
Takenori Kusumi,Haruko Takahashi,Ping Xu,Ping Xu,Toshiro Fukushima,Toshiro Fukushima,Yoshinori Asakawa,Yoshinori Asakawa,Toshihiro Hashimoto,Toshihiro Hashimoto,Yukiko Kan,Yukiko Kan,Yoshinobu Inouye,Yoshinobu Inouye +13 more
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TLDR
In this article, modified Mosher's method has been extended by use of 9-anthranylmethoxyacetic acid (9ATMA) and 2-naphthylmethoxynaphthymethylacetic acids (2NMA) instead of MTPA of the conventional method.About:
This article is published in Tetrahedron Letters.The article was published on 1994-06-20. It has received 81 citations till now. The article focuses on the topics: Absolute configuration & Carboxylic acid.read more
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The assignment of absolute configuration by NMR
TL;DR: In this paper, the application of (S)-1,10-binaphthyl-2,20-diol as NMR chiral solvating agent (CSA) for omeprazole, and three of its analogs (lanso-, panto-, and rabe-prazole) was investigated.
Journal ArticleDOI
New chiral anisotropic reagents for determining the absolute configuration of carboxylic acids
Yuriko Nagai,Takenori Kusumi +1 more
TL;DR: In this paper, the absolute configuration of carboxyl acids of type I was determined using enantiomers of phenylglycine dimethylamide (PGDA) and phenyl glycine methyl ester (PGME).
Journal ArticleDOI
A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates
TL;DR: In this paper, the addition of 2-(trimethylsilyloxy)furans to oxazolidinone enoates in the presence of hexafluoroisopropanol proceeded stereoselectively to give 4-substituted butenolides in good yields.
Journal ArticleDOI
The Modified Mosher’s Method and the Sulfoximine Method
TL;DR: In this article, the modified Mosher's method is applied to a variety of natural products possessing a secondary alcohol for determining their absolute configuration, and the method is described in detail.
Journal ArticleDOI
Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, methoxy-(2-naphthyl)acetic acid
TL;DR: The absolute configuration of yessotoxin (1), a potent diarrhetic toxin causative of shellfish poisoning, was determined by NMR-spectroscopy using a chiral anisotropic reagent, methoxy-(2-naphthyl)acetic acid (2NMA), which was applied to a monoacetate of bisdesulfated bisotoxin this paper.
References
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Journal ArticleDOI
High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids
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Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters
James A. Dale,Harry S. Mosher +1 more
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On the use of the O-methylmandelate ester for establishment of absolute configuration of secondary alcohols
Barry M. Trost,John L. Belletire,Stephen A. Godleski,Patrick G. McDougal,James M. Balkovec,John J. Baldwin,M. E. Christy,Gerald S. Ponticello,Sandor L. Varga,James P. Springer +9 more
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Correlation of configuration and fluorine-19 chemical shifts of .alpha.-methoxy-.alpha.-trifluoromethylphenyl acetate derivatives
Journal ArticleDOI
Elucidation of the absolute configurations of amino acids and amines by the modified mosher's method
TL;DR: In this paper, the modified Mosher's method was applied to the N -MTPA derivatives of several amino acid esters and acyclic amines and it was shown that this method may be generally used to determine the absolute configurations of the α-carbons of amino compounds of less than 1 mg amount.
Related Papers (5)
Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters
James A. Dale,Harry S. Mosher +1 more