Activation of hemiaminal ethers by chiral brønsted acids for facile access to enantioselective two-carbon homologation using eneearbamates

Masahiro Terada; Kyoko Machioka; Keiichi Sorimachi

doi:10.1002/anie.200805385

Activation of hemiaminal ethers by chiral brønsted acids for facile access to enantioselective two-carbon homologation using eneearbamates

Masahiro Terada, Kyoko Machioka, Keiichi Sorimachi

SCI - Chemistry

Tohoku University

Research output: Contribution to journal › Article › peer-review

101 Citations (Scopus)

Abstract

An enriching experience: Chiral phosphoric acids have been used to catalyze the title transformation for aromatic and aliphatic hemiaminal ethers. The process affords the corresponding products in good to high enantioselectivity (see scheme; Boc=tert-butoxycarbonyl, G=aromatic group). The method enables facile access to highly enantioenriched 1,3-diamine derivatives.

Original language	English
Pages (from-to)	2553-2556
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	14
DOIs	https://doi.org/10.1002/anie.200805385
Publication status	Published - 2009 Mar 23

Keywords

Asymmetric catalysis
Brønsted acids
Hemiaminal ethers
Homologation
Organocatalysis

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10.1002/anie.200805385

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AU - Sorimachi, Keiichi

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AB - An enriching experience: Chiral phosphoric acids have been used to catalyze the title transformation for aromatic and aliphatic hemiaminal ethers. The process affords the corresponding products in good to high enantioselectivity (see scheme; Boc=tert-butoxycarbonyl, G=aromatic group). The method enables facile access to highly enantioenriched 1,3-diamine derivatives.

KW - Asymmetric catalysis

KW - Brønsted acids

KW - Hemiaminal ethers

KW - Homologation

KW - Organocatalysis

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Activation of hemiaminal ethers by chiral brønsted acids for facile access to enantioselective two-carbon homologation using eneearbamates

Abstract

Keywords

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