Catalytic asymmetric aminoallylation of aldehydes: A catalytic enantioselective aza-cope rearrangement

Magnus Rueping; Andrey P. Antonchick

doi:10.1002/anie.200803610

Catalytic asymmetric aminoallylation of aldehydes: A catalytic enantioselective aza-cope rearrangement

Magnus Rueping^*, Andrey P. Antonchick

^*Corresponding author for this work

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

102 Scopus citations

Abstract

(Chemical Equation Presented) A condensation-rearrangement sequence forms the basis of a high-yielding route to chiral homoallylic amines from readily accessible aldehydes (see scheme). This transformation is both the first enantioselective Brønsted acid catalyzed sigmatropic rearrangement and the first example of a catalytic asymmetric aza-Cope rearrangement.

Original language	English (US)
Pages (from-to)	10090-10093
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	52
DOIs	https://doi.org/10.1002/anie.200803610
State	Published - Dec 15 2008
Externally published	Yes

Keywords

Allylation
Brønsted acids
Ion pairs
Organocatalysis
Sigmatropic rearrangement

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.200803610

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title = "Catalytic asymmetric aminoallylation of aldehydes: A catalytic enantioselective aza-cope rearrangement",

abstract = "(Chemical Equation Presented) A condensation-rearrangement sequence forms the basis of a high-yielding route to chiral homoallylic amines from readily accessible aldehydes (see scheme). This transformation is both the first enantioselective Br{\o}nsted acid catalyzed sigmatropic rearrangement and the first example of a catalytic asymmetric aza-Cope rearrangement.",

keywords = "Allylation, Br{\o}nsted acids, Ion pairs, Organocatalysis, Sigmatropic rearrangement",

author = "Magnus Rueping and Antonchick, {Andrey P.}",

year = "2008",

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doi = "10.1002/anie.200803610",

language = "English (US)",

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journal = "Angewandte Chemie - International Edition",

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T1 - Catalytic asymmetric aminoallylation of aldehydes

T2 - A catalytic enantioselective aza-cope rearrangement

AU - Rueping, Magnus

AU - Antonchick, Andrey P.

PY - 2008/12/15

Y1 - 2008/12/15

N2 - (Chemical Equation Presented) A condensation-rearrangement sequence forms the basis of a high-yielding route to chiral homoallylic amines from readily accessible aldehydes (see scheme). This transformation is both the first enantioselective Brønsted acid catalyzed sigmatropic rearrangement and the first example of a catalytic asymmetric aza-Cope rearrangement.

AB - (Chemical Equation Presented) A condensation-rearrangement sequence forms the basis of a high-yielding route to chiral homoallylic amines from readily accessible aldehydes (see scheme). This transformation is both the first enantioselective Brønsted acid catalyzed sigmatropic rearrangement and the first example of a catalytic asymmetric aza-Cope rearrangement.

KW - Allylation

KW - Brønsted acids

KW - Ion pairs

KW - Organocatalysis

KW - Sigmatropic rearrangement

UR - http://www.scopus.com/inward/record.url?scp=57749121489&partnerID=8YFLogxK

U2 - 10.1002/anie.200803610

DO - 10.1002/anie.200803610

M3 - Article

C2 - 19025749

AN - SCOPUS:57749121489

SN - 1433-7851

VL - 47

SP - 10090

EP - 10093

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

Catalytic asymmetric aminoallylation of aldehydes: A catalytic enantioselective aza-cope rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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