107836-65-7Relevant articles and documents
Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines
Jang, Hwanjong,Romiti, Filippo,Torker, Sebastian,Hoveyda, Amir H.
, p. 1269 - 1275 (2017)
There are many biologically active organic molecules that contain one or more nitrogen-containing moieties, and broadly applicable and efficient catalytic transformations that deliver them diastereoselectively and/or enantioselectively are much sought after. Various methods for enantioselective synthesis of α-secondary amines are available (for example, from additions to protected/activated aldimines), but those involving ketimines are much less common. There are no reported additions of carbon-based nucleophiles to unprotected/unactivated (or N-H) ketimines. Here, we report a catalytic, diastereo- and enantioselective three-component strategy for merging an N-H ketimine, a monosubstituted allene and B 2 (pin) 2, affording products in up to 95% yield, >98% diastereoselectivity and >99:1 enantiomeric ratio. The utility of the approach is highlighted by synthesis of the tricyclic core of a class of compounds that have been shown to possess anti-Alzheimer activity. Stereochemical models developed with the aid of density functional theory calculations, which account for the observed trends and levels of enantioselectivity, are presented.
A one-pot reductive amination of ketones to primary amines using borane-dimethyl sulfide complex
Johansson, Anders,Lindstedt, Eva-Lotte,Olsson, Thomas
, p. 351 - 353 (2007/10/03)
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