醛和α-蒎烯非对映选择性合成氧杂双环[3.3.1]壬烯：铁(III)聚集催化作用

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-02-28 DOI:10.1002/adsc.202401329

Sophi R. Todtz, Soumik Das, Paul M. Zimmerman, James J. Devery

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Diastereoselective Synthesis of Oxabicyclo[3.3.1]nonenes from Aldehydes and α-Pinene: Fe(III) Aggregate Catalysis

A challenge for the acid-mediated formation of oxabicyclo[3.3.1]nonenes is side product formation. Presented herein is a Lewis acid-catalyzed method towards these structures from aldehydes and α-pinene, forming the endo diastereomer exclusively. We include a proposal for the stereochemical reassignment of previously reported exo diastereomers supported by density functional theory (DFT) calculations, 1H NMR, and X-ray crystallography. The reactive system includes a range of aldehyde substrates. Experimental observations along with quantum chemical simulations suggest that an Fe(III)-aldehyde aggregate functions as the active catalyst.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.