Nucleophilic ring-opening of epoxides: trends in β-substituted alcohols synthesis

Nucleophilic ring-opening of epoxides: trends in β-substituted alcohols synthesis The present review deals with the ring-opening of epoxides by various carbon, nitrogen, oxygen, halogen, and sulfur-con- taining nucleophiles, which most of the resulting products are versatile intermediates in the synthesis of various biologically active compounds. The regioselectivity and environmentally benign nature of procedures for the synthesis of similar products have been also discussed in detail. Keywords Ring-opening of epoxides · Azidohydrins · Thiocyanohydrins · Cyanohydrins · β-Aminoalcohols · β-Nitroalcohols · β-Nitratoalcohols halohydrins · Aminolysis · Alcoholysis · Hydrolysis · Acetolysis Introduction occurs by an S 2 mechanism, and the less substituted carbon is the site of nucleophilic attack (Scheme 1). Epoxides are among the most useful synthetic intermediates Conversely, in acidic conditions ring-opening proceeds which can be used towards the synthesis of many pharma-via S 1 mechanism and the more substituted carbon is the ceuticals, fine chemicals, and biologically active compounds site of attack (Scheme 2). [1]. Their reactions are mainly accomplished because of the electrophilic character of the heterocyclic moiety as well as their ring strain. They have an inherent ring strain of Nucleophilic ring‑opening reaction approximately 27 kcal/mol associated with the three-mem- of epoxides bered heterocycle which provides sufficient driving force for the ring-opening event. Ring-opening reactions can proceed A large variety of nucleophiles such as carbon, nitrogen, by http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of the Iranian Chemical Society Springer Journals

Nucleophilic ring-opening of epoxides: trends in β-substituted alcohols synthesis

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Publisher
Springer Berlin Heidelberg
Copyright
Copyright © 2018 by Iranian Chemical Society
Subject
Chemistry; Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry
ISSN
1735-207X
eISSN
1735-2428
D.O.I.
10.1007/s13738-018-1400-5
Publisher site
See Article on Publisher Site

Abstract

The present review deals with the ring-opening of epoxides by various carbon, nitrogen, oxygen, halogen, and sulfur-con- taining nucleophiles, which most of the resulting products are versatile intermediates in the synthesis of various biologically active compounds. The regioselectivity and environmentally benign nature of procedures for the synthesis of similar products have been also discussed in detail. Keywords Ring-opening of epoxides · Azidohydrins · Thiocyanohydrins · Cyanohydrins · β-Aminoalcohols · β-Nitroalcohols · β-Nitratoalcohols halohydrins · Aminolysis · Alcoholysis · Hydrolysis · Acetolysis Introduction occurs by an S 2 mechanism, and the less substituted carbon is the site of nucleophilic attack (Scheme 1). Epoxides are among the most useful synthetic intermediates Conversely, in acidic conditions ring-opening proceeds which can be used towards the synthesis of many pharma-via S 1 mechanism and the more substituted carbon is the ceuticals, fine chemicals, and biologically active compounds site of attack (Scheme 2). [1]. Their reactions are mainly accomplished because of the electrophilic character of the heterocyclic moiety as well as their ring strain. They have an inherent ring strain of Nucleophilic ring‑opening reaction approximately 27 kcal/mol associated with the three-mem- of epoxides bered heterocycle which provides sufficient driving force for the ring-opening event. Ring-opening reactions can proceed A large variety of nucleophiles such as carbon, nitrogen, by

Journal

Journal of the Iranian Chemical SocietySpringer Journals

Published: May 28, 2018

References

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