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Diastereoselective Synthesis of 2‐(1,3‐Dioxolanes‐4‐yl)‐4 H ‐pyran‐4‐ones from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (sulfones) and Aldehydes Based on Tandem Cyclization‐Cycloaddition Strategy
Author(s) -
Zhang Jianfang,
Deng Guisheng,
Wang Jianbo
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900545
Subject(s) - chemistry , tandem , diazo , cycloaddition , pyran , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , materials science , composite material
In AgSbF 6 /Rh 2 (OAc) 4 /DCM system, two‐component reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoates (sulfones) and two equivalent of aldehydes provided easy access to 2‐(1,3‐dioxolanes‐4‐yl)‐4 H ‐pyran‐4‐ones. This represents the first method for generating the novel heterocyclic compounds. A possible mechanism is proposed to explain this result. The most significant features of the tandem cyclization are simple procedure, mild conditions and high diastereoselectivity.