Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 12, Issue 6, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300152
Keywords
Azadiene; DFT calculations; Domino reaction; Nazarov reagent; Spiro[4; 5]decane
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We developed a NaH-promoted domino reaction between an azadiene bearing an indene moiety and a Nazarov reagent, leading to the synthesis of various substituted spiro[4.5]decane derivatives with good yields and high diastereoselectivity via [4+2] cycloaddition. The reaction conditions are mild and exhibit broad substrate scope. Furthermore, gram-scale experiment and transformation of the product were successfully carried out. Finally, DFT calculations were performed to confirm the proposed reaction mechanism and analyze the observed diastereoselectivity.
A NaH-promoted domino reaction between azadiene bearing an indene moiety with Nazarov reagent was developed. A variety of spiro[4.5]decane derivatives were obtained via [4+2] cycloaddition with good yields and high diastereoselectivity. The domino strategy benefited from mild reaction conditions and very broad substrate scope. Furthermore, a gram-scale experiment and a transformation of the product were carried out. Lastly, density functional theory (DFT) calculations have been performed to verify the proposed reaction mechanism and analyze the observed diastereoselectivity.
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