The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

Eoin Gould; Tomas Lebl; Alexandra M. Z. Slawin; Mark Reid; Tony Davies; Andrew D. Smith

doi:10.1039/c3ob41719k

The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

Eoin Gould, Tomas Lebl, Alexandra M. Z. Slawin, Mark Reid, Tony Davies, Andrew D. Smith^*

^*Corresponding author for this work

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

Abstract

Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organo-catalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of beta-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.

Original language	English
Pages (from-to)	7877-7892
Number of pages	16
Journal	Organic & Biomolecular Chemistry
Volume	11
Issue number	45
DOIs	https://doi.org/10.1039/c3ob41719k
Publication status	Published - 7 Dec 2013

Keywords

DIELS-ALDER REACTION
ALPHA-ACYLOXYACROLEINS
ALPHA,BETA-UNSATURATED ALDEHYDES
DIAMINE SALTS
CATALYSIS
ACCELERATION
DERIVATIVES
EPOXIDATION
KETONES
DESIGN

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title = "The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis",

abstract = "Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organo-catalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of beta-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.",

keywords = "DIELS-ALDER REACTION, ALPHA-ACYLOXYACROLEINS, ALPHA,BETA-UNSATURATED ALDEHYDES, DIAMINE SALTS, CATALYSIS, ACCELERATION, DERIVATIVES, EPOXIDATION, KETONES, DESIGN",

author = "Eoin Gould and Tomas Lebl and Slawin, {Alexandra M. Z.} and Mark Reid and Tony Davies and Smith, {Andrew D.}",

year = "2013",

month = dec,

day = "7",

doi = "10.1039/c3ob41719k",

language = "English",

volume = "11",

pages = "7877--7892",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "45",

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TY - JOUR

T1 - The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

AU - Gould, Eoin

AU - Lebl, Tomas

AU - Slawin, Alexandra M. Z.

AU - Reid, Mark

AU - Davies, Tony

AU - Smith, Andrew D.

PY - 2013/12/7

Y1 - 2013/12/7

N2 - Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organo-catalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of beta-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.

AB - Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organo-catalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of beta-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.

KW - DIELS-ALDER REACTION

KW - ALPHA-ACYLOXYACROLEINS

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - DIAMINE SALTS

KW - CATALYSIS

KW - ACCELERATION

KW - DERIVATIVES

KW - EPOXIDATION

KW - KETONES

KW - DESIGN

U2 - 10.1039/c3ob41719k

DO - 10.1039/c3ob41719k

M3 - Article

SN - 1477-0520

VL - 11

SP - 7877

EP - 7892

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 45

ER -

The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

Abstract

Keywords

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