scholarly journals Stereoselective Synthesis of (–)-Heliannuol E by α-Selective ­Propargyl Substitution

Synlett ◽  
2021 ◽  
Author(s):  
Narihito Ogawa ◽  
Chihiro Uematsu ◽  
Yuichi Kobayashi
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis ◽  
Aromatic Group

AbstractThis paper describes a stereoselective synthesis of (–)-heliannuol E through intramolecular cyclization of a phenol mesylate. The introduction of the aromatic group was achieved by α-selective propargyl substitution of a propargylic phosphate.

Stereoselective Synthesis of Cyclic Ethers by SmI2-Induced Reductive Intramolecular Cyclization

2002 ◽  
Vol 31 (2) ◽  
pp. 148-149 ◽  
Author(s):  
Goh Matsuo ◽  
Hitomi Kadohama ◽  
Tadashi Nakata
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis ◽  
Cyclic Ethers

scholarly journals Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 36-45
Author(s):  
Sujit Sarkar ◽  
Namita Devi ◽  
Bikoshita Porashar ◽  
Santu Ruidas ◽  
Anil Saikia
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Prins Cyclization ◽  
Enol Ethers ◽  
Toluenesulfonic Acid

Intramolecular cyclization of enol ethers mediated by para-toluenesulfonic acid leads to substituted tetrahydropyrans in good to moderate yields. The reaction is diastereoselective.

Stereoselective synthesis of 1,3-disubstituted isoindolines via Rh(iii)-catalyzed tandem oxidative olefination–cyclization of 4-aryl cyclic sulfamidates

2016 ◽  
Vol 52 (23) ◽  
pp. 4286-4289 ◽  
Author(s):  
Se-Mi Son ◽  
Yeon Ji Seo ◽  
Hyeon-Kyu Lee
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis

Rh(iii)-catalyzed tandem ortho C–H activation/olefination of 4-aryl cyclic sulfamidates and subsequent intramolecular cyclization which lead to the stereoselective synthesis of trans-1,3-disubstituted isoindolines are reported.

Stereoselective Synthesis of 3-Substituted Tetrahydropyrazinoisoquinolines via Intramolecular Cyclization of Enantiomerically Enriched Dihydro-2H-pyrazines

2015 ◽  
Vol 17 (3) ◽  
pp. 398-401 ◽  
Author(s):  
Gianna Reginato ◽  
Maria Pia Catalani ◽  
Bernardo Pezzati ◽  
Romano Di Fabio ◽  
Andrea Bernardelli ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis

Stereoselective synthesis of dioxabicycles from 1-C-allyl-2-O-benzyl-glycosides — An intramolecular cyclization between 2-O-benzyl oxygen and the allyl double bond

2006 ◽  
Vol 84 (4) ◽  
pp. 597-602 ◽  
Author(s):  
An-Tai Wu ◽  
Tian Yi ◽  
Huawu Shao ◽  
Shih-Hsiung Wu ◽  
Wei Zou
Keyword(s):  
Double Bond ◽  
Intramolecular Cyclization ◽  
Stereoselective Synthesis ◽  
Carbonium Ion

Addition of a proton to the double bond of 1-C-allyl-O-benzylglycosides gave a 2′-carbonium ion, which in turn reacted intramolecularly, in a regio- and diastereo-selective manner, with the nucleophilic oxygen of the 2-O-benzyl group to form an oxonium intermediate. Subsequent cleavage of the benzyl C—O bond led to dioxabicycles in moderate yields. Surprisingly, opposite diastereoselectivities were observed from 1-C-allylglycofuranosides and 1-C-allylglycopyranosides, which produced 2,2′-trans- and 2,2′-cis-dioxabicycles, respectively.Key words: C-glycoside, olefin, cyclization, oxocarbonium, dioxabicycles.

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