Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate

Masahiro Terada; Kazuyo Soga; Norie Momiyama

doi:10.1002/anie.200800232

Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate

Masahiro Terada, Kazuyo Soga, Norie Momiyama

SCI - Chemistry

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

130 Citations (Scopus)

Abstract

(Chemical Equation Presented) Double interaction doesit: Highly enantio- and diastereoselective aza-ene-type reaction of glyoxylate with an enecarbamate is accomplished by using a binol-derived phosphoric acid catalyst (see scheme). DFT computational analysis revealed that two hydrogen bonds formed between the catalyst and the aldehyde are critical for the high enantioselectivity.

Original language	English
Pages (from-to)	4122-4125
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	22
DOIs	https://doi.org/10.1002/anie.200800232
Publication status	Published - 2008 May 19

Keywords

Asymmetric catalysis
Brønsted acids
Ene reactions
Phosphoric acids
Transition states

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200800232

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AU - Terada, Masahiro

AU - Soga, Kazuyo

AU - Momiyama, Norie

PY - 2008/5/19

Y1 - 2008/5/19

N2 - (Chemical Equation Presented) Double interaction doesit: Highly enantio- and diastereoselective aza-ene-type reaction of glyoxylate with an enecarbamate is accomplished by using a binol-derived phosphoric acid catalyst (see scheme). DFT computational analysis revealed that two hydrogen bonds formed between the catalyst and the aldehyde are critical for the high enantioselectivity.

AB - (Chemical Equation Presented) Double interaction doesit: Highly enantio- and diastereoselective aza-ene-type reaction of glyoxylate with an enecarbamate is accomplished by using a binol-derived phosphoric acid catalyst (see scheme). DFT computational analysis revealed that two hydrogen bonds formed between the catalyst and the aldehyde are critical for the high enantioselectivity.

KW - Asymmetric catalysis

KW - Brønsted acids

KW - Ene reactions

KW - Phosphoric acids

KW - Transition states

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Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate

Abstract

Keywords

ASJC Scopus subject areas

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