Dual In Situ Generation of Aliphatic Vinyl Ethers and Electron-Deficient ortho-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition: A Selective One-Pot Synthesis of 3-Alkylchromanes

Synlett ◽  
2020 ◽  
Vol 31 (12) ◽  
pp. 1197-1200 ◽  
Author(s):  
Yujiro Hoshino ◽  
Kiyoshi Honda ◽  
Kenta Tanaka ◽  
Ko Ueno ◽  
Yuta Tanaka ◽  
...  
Keyword(s):  
Biologically Active ◽  
Vinyl Ethers ◽  
Quinone Methides ◽  
One Pot ◽  
Inverse Electron Demand ◽  
One Pot Synthesis ◽  
In Situ Generation ◽  
Electron Demand

An inverse-electron-demand [4+2] cycloaddition of in situ generated aliphatic vinyl ethers and electron-deficient ortho-quinone methides (o-QMs) has been developed. The reaction of in situ generated aliphatic vinyl ethers with o-QMs afforded the corresponding 3-alkylchromanes with high stereo- and regioselectivities. The method provides a versatile access to functionalized 3-alkylchromanes and it constitutes a useful tool for the synthesis of biologically active chromanes.

Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho-Quinone Methides Generated In Situ

Synlett ◽  
2018 ◽  
Vol 30 (02) ◽  
pp. 189-192 ◽  
Author(s):  
Yujiro Hoshino ◽  
Kiyoshi Honda ◽  
Kenta Tanaka ◽  
Mami Kishimoto ◽  
Naoya Ohtsuka ◽  
...  
Keyword(s):  
Biologically Active ◽  
Quinone Methides ◽  
One Pot ◽  
One Pot Synthesis ◽  
Reaction Proceeds ◽  
Acidic Conditions ◽  
High Yields

A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho-quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.

Tandem inverse electron demand Diels–Alder, retro-Diels–Alder and intramolecular Diels–Alder sequences: one-pot synthesis of diaza-polycycles

Tetrahedron ◽  
2007 ◽  
Vol 63 (26) ◽  
pp. 6004-6014 ◽  
Author(s):  
William J. Bromley ◽  
Mairi Gibson ◽  
Stuart Lang ◽  
Steven A. Raw ◽  
Adrian C. Whitwood ◽  
...  
Keyword(s):  
Diels Alder ◽  
One Pot ◽  
Inverse Electron Demand ◽  
One Pot Synthesis ◽  
Electron Demand

scholarly journals One-pot synthesis of epoxides from benzyl alcohols and aldehydes

2018 ◽  
Vol 14 ◽  
pp. 2308-2312 ◽  
Author(s):  
Edwin Alfonzo ◽  
Jesse W L Mendoza ◽  
Aaron B Beeler
Keyword(s):  
One Pot ◽  
Sulfonium Salts ◽  
Benzyl Alcohols ◽  
One Pot Synthesis ◽  
Reaction Proceeds ◽  
In Situ Generation

A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

scholarly journals One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

2015 ◽  
Vol 11 ◽  
pp. 1265-1273 ◽  
Author(s):  
Mohammad Abbasi ◽  
Reza Khalifeh
Keyword(s):  
Conjugate Addition ◽  
Alkyl Halides ◽  
Displacement Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Organic Halides ◽  
Nucleophilic Displacement ◽  
In Situ Generation

An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.

One-pot synthesis of protected prostaglandins from alkynes and cyclopentenones. In situ generation of higher order cyanocuprates derived from alkenylzirconium intermediates

1990 ◽  
Vol 112 (20) ◽  
pp. 7441-7442 ◽  
Author(s):  
Kevin A. Babiak ◽  
James R. Behling ◽  
John H. Dygos ◽  
Kathleen T. McLaughlin ◽  
John S. Ng ◽  
...  
Keyword(s):  
Higher Order ◽  
One Pot ◽  
One Pot Synthesis ◽  
In Situ Generation
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