Organic Letters
Organic Letters
5 years ago

Diastereoselective α-Alkylation of Metallo Enamines Generated from N–C Axially Chiral Mebroqualone Derivatives

Diastereoselective α-Alkylation of Metallo Enamines Generated from N–C Axially Chiral Mebroqualone Derivatives
Mizuki Matsuoka, Alicja Wzorek, Osamu Kitagawa, Mitsuhiro Goto, Vadim A. Soloshonok
The reactions of various alkyl halides with the metallo enamines generated from racemic and optically pure N–C axially chiral mebroqualone derivatives were found to proceed with a synthetically attractive stereochemical outcome (up to 99% yield and up to dr = 26:1) allowing preparation of a structurally new type of pharmaceutically interesting compounds possessing elements of axial and central chirality.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00998

DOI: 10.1021/acs.orglett.7b00998

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