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

Mizuki Matsuoka, Mitsuhiro Goto, Alicja Wzorek, Vadim A. Soloshonok, Osamu Kitagawa

Research output: Contribution to journalArticle

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Abstract

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.

LanguageEnglish
Pages2650-2653
Number of pages4
JournalOrganic Letters
Volume19
Issue number10
DOIs
StatePublished - 2017 May 19

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Chirality
alkylation
Alkylation
chirality
halides
Derivatives
preparation

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Diastereoselective α-Alkylation of Metallo Enamines Generated from N-C Axially Chiral Mebroqualone Derivatives. / Matsuoka, Mizuki; Goto, Mitsuhiro; Wzorek, Alicja; Soloshonok, Vadim A.; Kitagawa, Osamu.

In: Organic Letters, Vol. 19, No. 10, 19.05.2017, p. 2650-2653.

Research output: Contribution to journalArticle

Matsuoka, Mizuki ; Goto, Mitsuhiro ; Wzorek, Alicja ; Soloshonok, Vadim A. ; Kitagawa, Osamu. / Diastereoselective α-Alkylation of Metallo Enamines Generated from N-C Axially Chiral Mebroqualone Derivatives. In: Organic Letters. 2017 ; Vol. 19, No. 10. pp. 2650-2653
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