Highly Enantioselective Asymmetric Hydrogenation of α-Phthalimide Ketone:  An Efficient Entry to Enantiomerically Pure Amino Alcohols

2004 ◽  
Vol 126 (6) ◽  
pp. 1626-1627 ◽  
Author(s):  
Aiwen Lei ◽  
Shulin Wu ◽  
Minsheng He ◽  
Xumu Zhang
Keyword(s):  
Asymmetric Hydrogenation ◽  
Amino Alcohols ◽  
Enantiomerically Pure

Direct Stereoselective Synthesis of Enantiomerically Pure anti-β-Amino Alcohols

2014 ◽  
Vol 79 (15) ◽  
pp. 6775-6782 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Osvaldo J. Donadel ◽  
Víctor S. Martín ◽  
José M. Padrón
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols ◽  
Enantiomerically Pure

Synthesis of novel chiral fluorescent sensors and their application in enantioselective discrimination of chiral carboxylic acids

2019 ◽  
Vol 43 (9-10) ◽  
pp. 340-346 ◽  
Author(s):  
Qiuhan Yu ◽  
Weiwen Lu ◽  
Zhiqiang Ding ◽  
Min Wei ◽  
Zhenya Dai
Keyword(s):  
Carboxylic Acids ◽  
Chiral Recognition ◽  
Amino Alcohols ◽  
Fluorescent Sensors ◽  
Enantiomerically Pure ◽  
Wide Range

Novel chiral fluorescent sensors are synthesized from a dibromide containing a tetraphenylethylene moiety and enantiomerically pure amino alcohols and an amine. The sensors are applied for the chiral recognition of a wide range of chiral carboxylic acids and related derivatives.

scholarly journals Regioselective and Stereodivergent Synthesis of Enantiomerically Pure Vic-Diamines from Chiral β-Amino Alcohols with 2-Pyridyl and 6-(2,2′-Bipyridyl) Moieties

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 727 ◽  
Author(s):  
Marzena Wosińska-Hrydczuk ◽  
Przemysław J. Boratyński ◽  
Jacek Skarżewski
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Ring Closure ◽  
Mitsunobu Reaction ◽  
Hydroxyl Group ◽  
Hydrazoic Acid ◽  
Enantiomerically Pure ◽  
Endocyclic Nitrogen Atom ◽  
Diastereomeric Mixture ◽  
Complete Series

In this report, we describe the synthetic elaboration of the easily available enantiomerically pure β-amino alcohols. Attempted direct substitution of the hydroxyl group by azido-functionality in the Mitsunobu reaction with hydrazoic acid was inefficient or led to a diastereomeric mixture. These outcomes resulted from the participation of aziridines. Intentionally performed internal Mitsunobu reaction of β-amino alcohols gave eight chiral aziridines in 45–82% yield. The structural and configuration identity of products was confirmed by NMR data compared to the DFT calculated GIAO values. For 1,2,3-trisubstituted aziridines slow configurational inversion at the endocyclic nitrogen atom was observed by NMR at room temperature. Moreover, when aziridine was titrated with Zn(OAc)2 under NMR control, only one of two N-epimers directly participated in complexation. The aziridines underwent ring opening with HN3 to form the corresponding azido amines as single regio- and diastereomers in 90–97% yield. Different results were obtained for 1,2-disubstituted and 1,2,3-trisubstituted aziridines. For the later aziridines ring closure and ring opening occurred at different carbon stereocenters, thus yielding products with two inverted configurations, compared to the starting amino alcohol. The 1,2-disubstituted aziridines produced azido amines of the same configuration as the starting β-amino alcohols. To obtain a complete series of diastereomeric vic-diamines, we converted the amino alcohols into cyclic sulfamidates, which reacted with sodium azide in SN2 reaction (25–58% overall yield). The azides obtained either way underwent the Staudinger reduction, giving a series of six new chiral vic-diamines of defined stereochemistries.

scholarly journals Simple Synthesis of Enantiomerically Pure C2-Symmetric Bisoxazolidines from Amino Alcohols and Formaldehyde

1999 ◽  
Vol 29 (1) ◽  
pp. 43-51 ◽  
Author(s):  
Carsten Bolm ◽  
Tsung-Hsun Chuang ◽  
Gerhard Raabe ◽  
Jim-Min Fang
Keyword(s):  
Amino Alcohols ◽  
Simple Synthesis ◽  
Enantiomerically Pure
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