Regioselective and Stereoselective Nucleophilic Ring Opening of Trifluoromethylated Cyclic Sulfates:  Asymmetric Synthesis of Both Enantiomers ofsyn-(3-Trifluoromethyl)isoserine

2004 ◽  
Vol 69 (16) ◽  
pp. 5486-5489 ◽  
Author(s):  
Zhong-Xing Jiang ◽  
Feng-Ling Qing
Keyword(s):  
Asymmetric Synthesis ◽  
Ring Opening ◽  
Cyclic Sulfates ◽  
Nucleophilic Ring Opening

scholarly journals Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine

ACS Omega ◽  
2018 ◽  
Vol 3 (12) ◽  
pp. 17562-17572 ◽  
Author(s):  
Gaurav Goswami ◽  
Navya Chauhan ◽  
Abhijit Mal ◽  
Subhomoy Das ◽  
Mowpriya Das ◽  
...  
Keyword(s):  
Ring Opening ◽  
Synthetic Route ◽  
Nucleophilic Ring Opening

scholarly journals (1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Ring Opening ◽  
Environmentally Friendly ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Excellent Yield ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

Stereochemistry of the nucleophilic ring-opening of activated bicyclo-[3.1.0]Hexanes.

1977 ◽  
Vol 18 (1) ◽  
pp. 109-112 ◽  
Author(s):  
Daiei Tunemoto ◽  
Nobuhiko Araki ◽  
Kiyosi Kondo
Keyword(s):  
Ring Opening ◽  
Nucleophilic Ring Opening
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