Synthesis of 2-Aryloxy-6-Methyl-4-Trichloromethyl-4h-1,3,2-Benzodioxaphosphorin 2-Oxides/Sulfides

Herein we report the asymmetric organocatalyzed method for the Friedel–Crafts reaction between activated phenols and trihaloacetaldehydes. A three‐phase screening including 41 compounds was employed to identify a catalyst structure based on 3,5‐dinitrobenzamide of 9‐amino‐epi‐cinchonidine as the lead catalytic molecule. Under the optimized reaction conditions, the above catalyst offered trihalohydroxyalkylated adducts in yields ranging from 26 to 92% and enantiomeric ratios within 69:31–99:1. The reaction scope was determined on 29 entries and several follow‐up transformations of the enantioenriched products were accomplished.

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Asymmetric Organocatalyzed Friedel–Crafts Reaction of Trihaloacetaldehydes and Phenols

Svestka

Otevřel

Bobáľ

2022

Adv Synth Catal

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A convenient synthesis of 2‐alkoxy‐2‐oxo‐1,4,2‐oxazaphosphinanes

Wang

Miao

Huang

et al. 2007

Heteroatom Chemistry

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Synthesis and Structure of O,O‐Diethyl N‐[(trans‐4‐Aryl‐5,5‐dimethyl‐2‐oxido‐2λ⁵‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates

Miao

Zhang

Cui

et al. 2007

Helvetica Chimica Acta

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A study on the synthesis of the novel N‐(cyclic phosphonate)‐substituted phosphoramidothioates, i.e., O,O‐diethyl N‐[(trans‐4‐aryl‐5,5‐dimethyl‐2‐oxido‐2λ5‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates 4a–l, from O,O‐diethyl phosphoramidothioate (1), a benzaldehyde or ketone 2, and a 1,3,2‐dioxaphosphorinane 2‐oxide 3 was carried out (Scheme 1 and Table 1). Some of their stereoisomers were isolated, and their structure was established. The presence of acetyl chloride was essential for this reaction and accelerated the process of intramolecular dehydration of intermediate 5 forming the corresponding Schiff base 7 (Scheme 2).

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Synthesis of 2-Aryloxy-6-Methyl-4-Trichloromethyl-4h-1,3,2-Benzodioxaphosphorin 2-Oxides/Sulfides

Cited by 8 publications

References 18 publications

Asymmetric Organocatalyzed Friedel–Crafts Reaction of Trihaloacetaldehydes and Phenols

Asymmetric Organocatalyzed Friedel–Crafts Reaction of Trihaloacetaldehydes and Phenols

A convenient synthesis of 2‐alkoxy‐2‐oxo‐1,4,2‐oxazaphosphinanes

Synthesis and Structure of O,O‐Diethyl N‐[(trans‐4‐Aryl‐5,5‐dimethyl‐2‐oxido‐2λ⁵‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates

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Synthesis of 2-Aryloxy-6-Methyl-4-Trichloromethyl-4h-1,3,2-Benzodioxaphosphorin 2-Oxides/Sulfides

Cited by 8 publications

References 18 publications

Asymmetric Organocatalyzed Friedel–Crafts Reaction of Trihaloacetaldehydes and Phenols

Asymmetric Organocatalyzed Friedel–Crafts Reaction of Trihaloacetaldehydes and Phenols

A convenient synthesis of 2‐alkoxy‐2‐oxo‐1,4,2‐oxazaphosphinanes

Synthesis and Structure of O,O‐Diethyl N‐[(trans‐4‐Aryl‐5,5‐dimethyl‐2‐oxido‐2λ5‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates

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Synthesis and Structure of O,O‐Diethyl N‐[(trans‐4‐Aryl‐5,5‐dimethyl‐2‐oxido‐2λ⁵‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates