Development of the first Brønsted acid assisted enantioselective Brønsted acid catalyzed direct Mannich reaction

Magnus Rueping; Erli Sugiono; Fenja R. Schoepke

doi:10.1055/s-2007-980369

Development of the first Brønsted acid assisted enantioselective Brønsted acid catalyzed direct Mannich reaction

Magnus Rueping^*, Erli Sugiono, Fenja R. Schoepke

^*Corresponding author for this work

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

89 Scopus citations

Abstract

We here describe the development of the first enantioselective Brønsted acid assisted chiral Brønsted acid catalyzed direct Mannich reaction of acetophenone with various aldimines. The reaction proceeds in the presence of a chiral and an achiral Brønsted acid which simultaneously activate the ketone and aldimine to give the corresponding P-amino ketones with good enantioselectivities and without the necessity of enolate preformation.

Original language	English (US)
Pages (from-to)	1441-1445
Number of pages	5
Journal	Synlett
Issue number	9
DOIs	https://doi.org/10.1055/s-2007-980369
State	Published - Jun 1 2007
Externally published	Yes

Keywords

BINOL-phosphate
Broønsted acid
Cooperative catalysis
Mannich reaction
Organocatalysis

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2007-980369

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title = "Development of the first Br{\o}nsted acid assisted enantioselective Br{\o}nsted acid catalyzed direct Mannich reaction",

abstract = "We here describe the development of the first enantioselective Br{\o}nsted acid assisted chiral Br{\o}nsted acid catalyzed direct Mannich reaction of acetophenone with various aldimines. The reaction proceeds in the presence of a chiral and an achiral Br{\o}nsted acid which simultaneously activate the ketone and aldimine to give the corresponding P-amino ketones with good enantioselectivities and without the necessity of enolate preformation.",

keywords = "BINOL-phosphate, Bro{\o}nsted acid, Cooperative catalysis, Mannich reaction, Organocatalysis",

author = "Magnus Rueping and Erli Sugiono and Schoepke, {Fenja R.}",

year = "2007",

month = jun,

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doi = "10.1055/s-2007-980369",

language = "English (US)",

pages = "1441--1445",

journal = "Synlett",

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publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Development of the first Brønsted acid assisted enantioselective Brønsted acid catalyzed direct Mannich reaction

AU - Rueping, Magnus

AU - Sugiono, Erli

AU - Schoepke, Fenja R.

PY - 2007/6/1

Y1 - 2007/6/1

N2 - We here describe the development of the first enantioselective Brønsted acid assisted chiral Brønsted acid catalyzed direct Mannich reaction of acetophenone with various aldimines. The reaction proceeds in the presence of a chiral and an achiral Brønsted acid which simultaneously activate the ketone and aldimine to give the corresponding P-amino ketones with good enantioselectivities and without the necessity of enolate preformation.

AB - We here describe the development of the first enantioselective Brønsted acid assisted chiral Brønsted acid catalyzed direct Mannich reaction of acetophenone with various aldimines. The reaction proceeds in the presence of a chiral and an achiral Brønsted acid which simultaneously activate the ketone and aldimine to give the corresponding P-amino ketones with good enantioselectivities and without the necessity of enolate preformation.

KW - BINOL-phosphate

KW - Broønsted acid

KW - Cooperative catalysis

KW - Mannich reaction

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=34250760386&partnerID=8YFLogxK

U2 - 10.1055/s-2007-980369

DO - 10.1055/s-2007-980369

M3 - Article

AN - SCOPUS:34250760386

SN - 0936-5214

SP - 1441

EP - 1445

JO - Synlett

JF - Synlett

IS - 9

ER -

Development of the first Brønsted acid assisted enantioselective Brønsted acid catalyzed direct Mannich reaction

Abstract

Keywords

ASJC Scopus subject areas

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