Structure-reactivity studies of simple 4-hydroxyprolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

John Watts; Lien Luu; Vickie McKee; Ed Carey; Fintan Kelleher

doi:10.1002/adsc.201100028

Structure-reactivity studies of simple 4-hydroxyprolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

John Watts, Lien Luu, Vickie McKee, Ed Carey, Fintan Kelleher

School of Chemical and BioPharmaceutical Science

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

Abstract

A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% ee for syn). Furthermore, the use of low catalyst loadings (5mol%) and a low aldehyde molar excess (1.5equivalents) were achieved.

Original language	English
Pages (from-to)	1035-1042
Number of pages	8
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	6
DOIs	https://doi.org/10.1002/adsc.201100028
Publication status	Published - 16 Apr 2012

Keywords

DFT calculations
Michael addition reaction
organocatalysis
prolinamide
structure-reactivity relationships

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10.1002/adsc.201100028

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abstract = "A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% ee for syn). Furthermore, the use of low catalyst loadings (5mol%) and a low aldehyde molar excess (1.5equivalents) were achieved.",

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AU - Watts, John

AU - Luu, Lien

AU - McKee, Vickie

AU - Carey, Ed

AU - Kelleher, Fintan

PY - 2012/4/16

Y1 - 2012/4/16

N2 - A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% ee for syn). Furthermore, the use of low catalyst loadings (5mol%) and a low aldehyde molar excess (1.5equivalents) were achieved.

AB - A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% ee for syn). Furthermore, the use of low catalyst loadings (5mol%) and a low aldehyde molar excess (1.5equivalents) were achieved.

KW - DFT calculations

KW - Michael addition reaction

KW - organocatalysis

KW - prolinamide

KW - structure-reactivity relationships

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DO - 10.1002/adsc.201100028

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VL - 354

SP - 1035

EP - 1042

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 6

ER -

Structure-reactivity studies of simple 4-hydroxyprolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

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Keywords

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