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Cyclization of olefinic alcohol by benzeneselenenyl triflate

✍ Scribed by Shizuaki Murata; Toshiyasu Suzuki

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
126 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cyclization

of alkenol by an electrophilic organoselenium reagent is the important procedure for the synthesis of cyclic ether. 1 However previous reagents for oxyselenation do not always give satisfactory results, e.9. low reactivity, poor selectivity, and addition of the halide ion.

Recently we reported synthetic utilities of superelectrophilic benzeneselenenyl triflate

(1) for selenolactonization of the unsaturated carboxylic acid. 2 Described herein is its application for cyclization of the olefinic alcohol.

Reaction of 5-and 6-hydroxyalkene 2a-2h with 1 equivalent of 1 (PhSeOTf)

proceeded in dichloromethane at -78 -0 'C to give exo-cyclized3 tetrahydrofuran or -pyran derivatives 3a-3h, respectively. Results are summarized in

πŸ“œ SIMILAR VOLUMES

Stereoselective Cyclization of 4-Substit
Stereoselective Cyclization of 4-Substituted 5-Hexen-1-ols and Related Compounds by Benzeneselenenyl Triflate
✍ Inoue, Hirohumi ;Murata, Shizuaki ;Suzuki, Toshiyasu πŸ“‚ Article πŸ“… 1994 πŸ› John Wiley and Sons 🌐 English βš– 953 KB

## Abstract Oxyselenylation of 4‐substituted 5‐hexen‐1‐ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular __exo__ cyclization stereoselectively to give 3‐substituted __trans__‐ or __cis__‐2‐(phenylselenenylmethyl)tetrahydropyrans 3. Formation of the __trans__ isomers i

Regioselectivity in Cyclofunctionalizati
Regioselectivity in Cyclofunctionalization of Olefinic Alcohols with Benzeneselenenyl Halides at Different Temperatures[1 – 4]
✍ Konstantinovic, Stanimir ;Bugarčič, Zorica ;Milosavljevič, Slobodan ;Schroth, Ge πŸ“‚ Article πŸ“… 1992 πŸ› John Wiley and Sons 🌐 English βš– 719 KB

## Abstract The regioselectivity in cyclofunctionalization of some acyclic olefinic alcohols with benzeneselenenyl halides (PhSeCl and PhSeBr) at different temperatures (βˆ’78^Β°^C, O^Β°^C and room temperature) is investigated. It has been found that Ξ”^4^‐ and Ξ”^5^‐ alkenols are converted into five‐ an