Diastereoselective Synthesis of Dearomatic 2‐oxa‐7‐azaspiro[4.5]decane Derivatives through Gold and Palladium Relay Catalytic Tandem Cyclization of Enynamides with Vinyl Benzoxazinanones DOI
Jiaming Xu, Yanfeng Gao, Xin Gao

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(22), С. 4778 - 4785

Опубликована: Авг. 14, 2024

Abstract We present a diastereoselective Au/Pd relay catalytic tandem cyclization reaction to produce dearomatic 2‐oxa‐7‐azaspiro[4.5]decane derivatives under mild conditions. This process involves generating furan‐derived azadiene from readily available enynamide, followed by [2+4] cycloaddition with Pd‐ π ‐allyl dipole decarboxylated vinyl benzoxazinanone. Our method efficiently constructs the spiro[4.5]decane skeleton, achieving yields ranging 31–97% and diastereoselectivities 6:1 dr >20:1 across 34 examples. research introduces new sites for azadienes as 1,2‐dipoles offers reliable approach constructing oxa‐azaspiro[4.5]decane frameworks.

Язык: Английский

Diastereoselective Synthesis of Dearomatic 2‐oxa‐7‐azaspiro[4.5]decane Derivatives through Gold and Palladium Relay Catalytic Tandem Cyclization of Enynamides with Vinyl Benzoxazinanones DOI
Jiaming Xu, Yanfeng Gao, Xin Gao

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(22), С. 4778 - 4785

Опубликована: Авг. 14, 2024

Abstract We present a diastereoselective Au/Pd relay catalytic tandem cyclization reaction to produce dearomatic 2‐oxa‐7‐azaspiro[4.5]decane derivatives under mild conditions. This process involves generating furan‐derived azadiene from readily available enynamide, followed by [2+4] cycloaddition with Pd‐ π ‐allyl dipole decarboxylated vinyl benzoxazinanone. Our method efficiently constructs the spiro[4.5]decane skeleton, achieving yields ranging 31–97% and diastereoselectivities 6:1 dr >20:1 across 34 examples. research introduces new sites for azadienes as 1,2‐dipoles offers reliable approach constructing oxa‐azaspiro[4.5]decane frameworks.

Язык: Английский

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