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

doi:10.1021/acs.orglett.7b00998

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 journal › Article › peer-review

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2650-2653
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00998
Publication status	Published - 2017 May 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b00998

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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.",

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AU - Matsuoka, Mizuki

AU - Goto, Mitsuhiro

AU - Wzorek, Alicja

AU - Soloshonok, Vadim A.

AU - Kitagawa, Osamu

PY - 2017/5/19

Y1 - 2017/5/19

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AB - 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.

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

Abstract

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