An enantioselective chiral Brønsted acid catalyzed imino-azaenamine reaction

Magnus Rueping; Erli Sugiono; Thomas Theissmann; Alexander Kuenkel; Angela Kǒckritz; Anahit Pews-Davtyan; Navid Nemati; Matthias Beller

doi:10.1021/ol063112p

An enantioselective chiral Brønsted acid catalyzed imino-azaenamine reaction

Magnus Rueping^*, Erli Sugiono, Thomas Theissmann, Alexander Kuenkel, Angela Kǒckritz, Anahit Pews-Davtyan, Navid Nemati, Matthias Beller

^*Corresponding author for this work

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

106 Scopus citations

Abstract

(Chemical Equation Presented) The enantioselective Brønsted acid catalyzed addition of methyleneaminopyrrolidine to N-Boc imines has been achieved in the presence of chiral phosphoric acids derived from 3,3′-di(phenanthryl)-H8-BINOL. The corresponding aminohydrazones have been isolated in good yields with enantiomeric excesses up to 90%.

Original language	English (US)
Pages (from-to)	1065-1068
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	6
DOIs	https://doi.org/10.1021/ol063112p
State	Published - Mar 15 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol063112p

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title = "An enantioselective chiral Br{\o}nsted acid catalyzed imino-azaenamine reaction",

abstract = "(Chemical Equation Presented) The enantioselective Br{\o}nsted acid catalyzed addition of methyleneaminopyrrolidine to N-Boc imines has been achieved in the presence of chiral phosphoric acids derived from 3,3′-di(phenanthryl)-H8-BINOL. The corresponding aminohydrazones have been isolated in good yields with enantiomeric excesses up to 90%.",

author = "Magnus Rueping and Erli Sugiono and Thomas Theissmann and Alexander Kuenkel and Angela Kǒckritz and Anahit Pews-Davtyan and Navid Nemati and Matthias Beller",

year = "2007",

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day = "15",

doi = "10.1021/ol063112p",

language = "English (US)",

volume = "9",

pages = "1065--1068",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - An enantioselective chiral Brønsted acid catalyzed imino-azaenamine reaction

AU - Rueping, Magnus

AU - Sugiono, Erli

AU - Theissmann, Thomas

AU - Kuenkel, Alexander

AU - Kǒckritz, Angela

AU - Pews-Davtyan, Anahit

AU - Nemati, Navid

AU - Beller, Matthias

PY - 2007/3/15

Y1 - 2007/3/15

N2 - (Chemical Equation Presented) The enantioselective Brønsted acid catalyzed addition of methyleneaminopyrrolidine to N-Boc imines has been achieved in the presence of chiral phosphoric acids derived from 3,3′-di(phenanthryl)-H8-BINOL. The corresponding aminohydrazones have been isolated in good yields with enantiomeric excesses up to 90%.

AB - (Chemical Equation Presented) The enantioselective Brønsted acid catalyzed addition of methyleneaminopyrrolidine to N-Boc imines has been achieved in the presence of chiral phosphoric acids derived from 3,3′-di(phenanthryl)-H8-BINOL. The corresponding aminohydrazones have been isolated in good yields with enantiomeric excesses up to 90%.

UR - http://www.scopus.com/inward/record.url?scp=33947574500&partnerID=8YFLogxK

U2 - 10.1021/ol063112p

DO - 10.1021/ol063112p

M3 - Article

C2 - 17305351

AN - SCOPUS:33947574500

SN - 1523-7060

VL - 9

SP - 1065

EP - 1068

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

An enantioselective chiral Brønsted acid catalyzed imino-azaenamine reaction

Abstract

ASJC Scopus subject areas

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