Chiral Brøsted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction

Magnus Rueping; Winai Ieawsuwan; Audrey P. Antonchick; Boris J. Nachtsheim

doi:10.1002/anie.200604809

Chiral Brøsted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction

Magnus Rueping^*, Winai Ieawsuwan, Audrey P. Antonchick, Boris J. Nachtsheim

^*Corresponding author for this work

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

266 Scopus citations

Abstract

(Chemical Equation Presented) Low catalyst loadings, high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five-membered rings with a chiral Bransted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.

Original language	English (US)
Pages (from-to)	2097-2100
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	12
DOIs	https://doi.org/10.1002/anie.200604809
State	Published - 2007
Externally published	Yes

Keywords

Binol phosphate
Brønsted acids
Electrocyclization
Ion-pair catalysis
Nazarov cyclization

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200604809

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title = "Chiral Br{\o}sted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction",

abstract = "(Chemical Equation Presented) Low catalyst loadings, high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five-membered rings with a chiral Bransted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.",

keywords = "Binol phosphate, Br{\o}nsted acids, Electrocyclization, Ion-pair catalysis, Nazarov cyclization",

author = "Magnus Rueping and Winai Ieawsuwan and Antonchick, {Audrey P.} and Nachtsheim, {Boris J.}",

year = "2007",

doi = "10.1002/anie.200604809",

language = "English (US)",

volume = "46",

pages = "2097--2100",

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T1 - Chiral Brøsted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction

AU - Rueping, Magnus

AU - Ieawsuwan, Winai

AU - Antonchick, Audrey P.

AU - Nachtsheim, Boris J.

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) Low catalyst loadings, high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five-membered rings with a chiral Bransted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.

AB - (Chemical Equation Presented) Low catalyst loadings, high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five-membered rings with a chiral Bransted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.

KW - Binol phosphate

KW - Brønsted acids

KW - Electrocyclization

KW - Ion-pair catalysis

KW - Nazarov cyclization

UR - http://www.scopus.com/inward/record.url?scp=34250725648&partnerID=8YFLogxK

U2 - 10.1002/anie.200604809

DO - 10.1002/anie.200604809

M3 - Article

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AN - SCOPUS:34250725648

SN - 1433-7851

VL - 46

SP - 2097

EP - 2100

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

Chiral Brøsted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction

Abstract

Keywords

ASJC Scopus subject areas

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