Templated assembly of medium cyclic ethers via exo-trig nucleophilic cyclization of cyclopropenes

2016 ◽  
Vol 52 (47) ◽  
pp. 7494-7496 ◽  
Author(s):  
Bassam K. Alnasleh ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Nucleophilic Addition ◽  
Cyclic Ethers ◽  
Novel Method ◽  
Medium Rings ◽  
Nucleophilic Cyclization

A novel method for the assembly of medium heterocycles via an intramolecular nucleophilic addition to cyclopropenes is described. The exo-trig nucleophilic cyclizations were shown to proceed very efficiently and in a highly diastereoselective fashion affording cis-fused bicyclic products possessing 7 to 10-membered medium rings; starting from a diastereomeric mixtures of bromocyclopropanes.

scholarly journals Nucleophilic Addition of Organozinc Reagents to 2-Sulfonyl Cyclic Ethers: Stereoselective Synthesis of Manassantins A and B

2009 ◽  
Vol 11 (7) ◽  
pp. 1671-1671
Author(s):  
Hyoungsu Kim ◽  
Amanda C. Kasper ◽  
Eui Jung Moon ◽  
Yongho Park ◽  
Ceshea M. Wooten ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Cyclic Ethers ◽  
Organozinc Reagents

scholarly journals An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3778 ◽  
Author(s):  
Qili Lu ◽  
Dipesh S. Harmalkar ◽  
Yongseok Choi ◽  
Kyeong Lee
Keyword(s):  
Natural Products ◽  
Biologically Active ◽  
Synthetic Methods ◽  
Cyclic Ethers ◽  
Considerable Effort ◽  
Oxygen Heterocycles ◽  
Broad Array ◽  
Synthetic Intermediates ◽  
Medium Rings ◽  
Saturated Oxygen

Saturated oxygen heterocycles are widely found in a broad array of natural products and other biologically active molecules. In medicinal chemistry, small and medium rings are also important synthetic intermediates since they can undergo ring-opening and -expansion reactions. These applications have driven numerous studies on the synthesis of oxygen-containing heterocycles and considerable effort has been devoted toward the development of methods for the construction of saturated oxygen heterocycles. This paper provides an overview of the biological roles and synthetic strategies of saturated cyclic ethers, covering some of the most studied and newly discovered related natural products in recent years. This paper also reports several promising and newly developed synthetic methods, emphasizing 3–7 membered rings.

Preparation of useful building blocks, α-iodo- and bromoalkanols from cyclic ethers using the Dowex H+/NaX (X = I, Br) approach

RSC Advances ◽  
2016 ◽  
Vol 6 (19) ◽  
pp. 15937-15940 ◽  
Author(s):  
Petri A. Turhanen ◽  
Jouko J. Vepsäläinen
Keyword(s):  
Building Blocks ◽  
Cyclic Ethers ◽  
Synthetic Chemistry ◽  
Complex Molecules ◽  
Novel Method

Novel method for preparation of α-iodo- and bromoalkanols directly from cyclic ethers has been developed. Prepared compounds are highly important building blocks in synthetic chemistry for the preparation of more complex molecules.

Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes

2020 ◽  
Vol 56 (78) ◽  
pp. 11621-11624
Author(s):  
Yanbin Zhang ◽  
Ruiwen Jin ◽  
Guangxing Pan ◽  
Hao Guo
Keyword(s):  
Nucleophilic Addition ◽  
Nucleophilic Cyclization

Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic cyclization of alkynes using non-nucleophilic alkyls as the nucleophile is reported.

Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8-endo-trig Nucleophilic Cyclization of Cyclopropenes

2016 ◽  
Vol 18 (24) ◽  
pp. 6272-6275 ◽  
Author(s):  
Pavel Ryabchuk ◽  
Jonathon P. Matheny ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Chiral Medium ◽  
Cyclic Ethers ◽  
Nucleophilic Cyclization
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