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Synfacts 2025; 21(07): 726
DOI: 10.1055/a-2601-4057
Organo- and Biocatalysis

Stereoselective Access to Noradamantane Derivatives

Contributor(s):
Benjamin List 
,
Nils Frank 
Daskalakis K, Umekubo N, Indu S, Kawauchi G, Taniguchi T, Monde K, Hayashi Y *. Tohoku University, Sendai, Japan
Asymmetric Synthesis of Noradamantane Scaffolds via Diphenylprolinol Silyl Ether-Mediated Domino Michael/Epimerization/Michael (or Aldol)/1,2-Addition Reactions.

Angew. Chem. Int. Ed. 2025;
DOI: 10.1002/anie.202500378
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Keywords

noradamantanes - domino reaction - Michael reaction - prolinols

Significance

Hayashi and co-workers present a synthesis of noradamantanes that employs a diphenylprolinol silyl ether organocatalyst. The domino reaction proceeds with excellent stereoselectivity (91:9 to 99.5:0.5 er) and yield (76−93 %), and establishes six stereocenters, of which five are completely controlled.


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Comment

Synthetic strategies towards noradamantane scaffolds are cumbersome and underdeveloped. This methodology is a valuable addition to the construction of cage-like compounds, with high importance for “escape-from-flatland” drug discovery campaigns.


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Publication History

Article published online:
23 June 2025

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