Synthesis of tetrasubstituted 1-silyloxy-3-aminobutadienes and chemistry beyond Diels–Alder reactions

Xijian Li, Siyu Peng, Li Li and Yong Huang ()
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Xijian Li: Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School
Siyu Peng: Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School
Li Li: Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School
Yong Huang: Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: Abstract Electron-rich dienes have revolutionized the synthesis of complex compounds since the discovery of the legendary Diels–Alder cycloaddition reaction. This highly efficient bond-forming process has served as a fundamental strategy to assemble many structurally formidable molecules. Amino silyloxy butadienes are arguably the most reactive diene species that are isolable and bottleable. Since the pioneering discovery by Rawal, 1-amino-3-silyloxybutadienes have been found to undergo cycloaddition reactions with unparalleled mildness, leading to significant advances in both asymmetric catalysis and total synthesis of biologically active natural products. In sharp contrast, this class of highly electron-rich conjugated olefins has not been studied in non-cycloaddition reactions. Here we report a simple synthesis of tetrasubstituted 1-silyloxy-3-aminobutadienes, a complementarily substituted Rawal’s diene. This family of molecules is found to undergo a series of intriguing chemical transformations orthogonal to cycloaddition reactions. Structurally diverse polysubstituted ring architectures are established in one step from these dienes.

Date: 2015
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DOI: 10.1038/ncomms7913

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