Multicomponent Hosomi-Sakurai Reaction on Isosorbide Derivatives

Area of Science:

• Organic Chemistry
• Green Chemistry
• Materials Science

Background:

• Isosorbide, a bio-based platform chemical, offers a sustainable scaffold for novel material synthesis.
• Multicomponent reactions like the Hosomi-Sakurai reaction are powerful tools for constructing complex molecules efficiently.

Purpose of the Study:

• To optimize the Hosomi-Sakurai reaction for monoprotected isosorbide derivatives.
• To explore the synthesis of novel isosorbide-aldehyde conjugates with potential applications in materials science.

Main Methods:

• Synthesis of trimethylsilyl ethers of monoprotected isosorbide derivatives.
• Application of the Hosomi-Sakurai reaction using allyl trimethylsilane and various aldehydes.
• Catalysis using trimethylsilyl triflate.

Main Results:

• Optimal reaction conditions identified using TMS ethers of the endo-OH group.
• Tert-butyldiphenylsilyl ether demonstrated superior performance as a protecting group.
• Good yields and high diastereoselectivities achieved with aromatic and aliphatic aldehydes, with noted exceptions for sterically hindered or electron-poor aromatic aldehydes.

Conclusions:

• The study establishes an efficient method for synthesizing isosorbide-aldehyde conjugates.
• The developed method provides access to novel bio-based materials with stable ether linkages.
• This work advances the utilization of isosorbide in sustainable chemical synthesis.