Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

R Robiette; M Conza; VK Aggarwal

doi:10.1039/b516926g

Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

R Robiette, M Conza, VK Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

37 Citations (Scopus)

Abstract

Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.

Original language	English
Pages (from-to)	621-623
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	4
Issue number	4
DOIs	https://doi.org/10.1039/b516926g
Publication status	Published - 21 Feb 2006

Keywords

IN-SITU GENERATION
ORGANOCATALYTIC CYCLOPROPANATION
CARBONYL-COMPOUNDS
DIAZO-COMPOUNDS
SULFUR YLIDES
SCOPE

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title = "Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes",

abstract = "Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.",

keywords = "IN-SITU GENERATION, ORGANOCATALYTIC CYCLOPROPANATION, CARBONYL-COMPOUNDS, DIAZO-COMPOUNDS, SULFUR YLIDES, SCOPE",

author = "R Robiette and M Conza and VK Aggarwal",

year = "2006",

month = feb,

day = "21",

doi = "10.1039/b516926g",

language = "English",

volume = "4",

pages = "621--623",

journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

AU - Robiette, R

AU - Conza, M

AU - Aggarwal, VK

PY - 2006/2/21

Y1 - 2006/2/21

N2 - Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.

AB - Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.

KW - IN-SITU GENERATION

KW - ORGANOCATALYTIC CYCLOPROPANATION

KW - CARBONYL-COMPOUNDS

KW - DIAZO-COMPOUNDS

KW - SULFUR YLIDES

KW - SCOPE

U2 - 10.1039/b516926g

DO - 10.1039/b516926g

M3 - Article (Academic Journal)

SN - 1477-0520

VL - 4

SP - 621

EP - 623

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 4

ER -

Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

Abstract

Keywords

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