ChemInform Abstract: Synthesis of Enantiopure 1,2-Azido and 1,2-Amino Alcohols via Regio- and Stereoselective Ring-Opening of Enantiopure Epoxides by Sodium Azide in Hot Water.

ChemInform ◽  
2016 ◽  
Vol 47 (24) ◽  
Author(s):  
Hai-Yang Wang ◽  
Kun Huang ◽  
Melvin De Jesus ◽  
Sandraliz Espinosa ◽  
Luis E. Pinero-Santiago ◽  
...  
Keyword(s):  
Sodium Azide ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Hot Water ◽  
Enantiopure Epoxides

scholarly journals Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water

2016 ◽  
Vol 27 (2-3) ◽  
pp. 91-100 ◽  
Author(s):  
Hai-Yang Wang ◽  
Kun Huang ◽  
Melvin De Jesús ◽  
Sandraliz Espinosa ◽  
Luis E. Piñero-Santiago ◽  
...  
Keyword(s):  
Sodium Azide ◽  
Ring Opening ◽  
Amino Alcohols ◽  
Hot Water ◽  
Enantiopure Epoxides

Synthesis of β-amino alcohols by regioselective ring opening of arylepoxides with anilines catalyzed by cobaltous chloride

2004 ◽  
Vol 45 (44) ◽  
pp. 8253-8256 ◽  
Author(s):  
Govindarajan Sundararajan ◽  
Kari Vijayakrishna ◽  
Babu Varghese
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Cobaltous Chloride

Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity

2018 ◽  
Vol 54 (92) ◽  
pp. 12998-13001 ◽  
Author(s):  
Michelle Lee ◽  
Jessica R. Lamb ◽  
Maria J. Sanford ◽  
Anne M. LaPointe ◽  
Geoffrey W. Coates
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Nucleophilic Ring Opening

We report the nucleophilic ring opening of unsymmetrical trans-epoxides to β-amino alcohols with catalyst-controlled regioselectivity.

scholarly journals Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines

2007 ◽  
Vol 2 (2) ◽  
pp. 1934578X0700200
Author(s):  
Suchitra Bhatt ◽  
Sandip K. Nayak
Keyword(s):  
Ambient Temperature ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Amino Alcohols ◽  
Azide Ion ◽  
Ring Opening Of Epoxides ◽  
Lewis Acid Catalyst

Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.

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 An efficient and atom-economical route to N-aryl amino alcohols from primary amines

RSC Advances ◽  
2018 ◽  
Vol 8 (60) ◽  
pp. 34304-34308 ◽  
Author(s):  
Zhen Xiao ◽  
Juanjuan Li ◽  
Qiang Yue ◽  
Qian Zhang ◽  
Dong Li
Keyword(s):  
Ring Opening ◽  
Amino Alcohols ◽  
Primary Amines ◽  
Ring Opening Reaction ◽  
Novel Method

A novel method for generation of N-aryl amino alcohols from N,N-disubstituted picolinamides through reduction/ring-opening reaction with NaBH4 was developed.

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