Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

Fintan Kelleher; Sinead Kelly; John Watts; Vickie McKee

doi:10.1016/j.tet.2010.03.002

Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

Fintan Kelleher, Sinead Kelly, John Watts, Vickie McKee

School of Chemical and BioPharmaceutical Science

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

Abstract

l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol %) and a low aldehyde molar excess (1.5 M equiv) were achieved.

Original language	English
Pages (from-to)	3525-3536
Number of pages	12
Journal	Tetrahedron
Volume	66
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2010.03.002 https://doi.org/10.1016/j.tet.2010.03.002
Publication status	Published - 8 May 2010

Keywords

Asymmetric organocatalysis
Michael addition reaction
Spirolactam
α-Methyl prolinamide

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title = "Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins",

abstract = "l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol \%) and a low aldehyde molar excess (1.5 M equiv) were achieved.",

keywords = "Asymmetric organocatalysis, Michael addition reaction, Spirolactam, α-Methyl prolinamide",

author = "Fintan Kelleher and Sinead Kelly and John Watts and Vickie McKee",

year = "2010",

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doi = "10.1016/j.tet.2010.03.002",

language = "English",

volume = "66",

pages = "3525--3536",

journal = "Tetrahedron",

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TY - JOUR

T1 - Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

AU - Kelleher, Fintan

AU - Kelly, Sinead

AU - Watts, John

AU - McKee, Vickie

PY - 2010/5/8

Y1 - 2010/5/8

N2 - l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol %) and a low aldehyde molar excess (1.5 M equiv) were achieved.

AB - l-Proline derived spirolactams and α-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol %) and a low aldehyde molar excess (1.5 M equiv) were achieved.

KW - Asymmetric organocatalysis

KW - Michael addition reaction

KW - Spirolactam

KW - α-Methyl prolinamide

UR - https://www.scopus.com/pages/publications/77950593254

U2 - 10.1016/j.tet.2010.03.002

DO - 10.1016/j.tet.2010.03.002

M3 - Article

AN - SCOPUS:77950593254

SN - 0040-4020

VL - 66

SP - 3525

EP - 3536

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Structure-reactivity relationships of l-proline derived spirolactams and α-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

Abstract

Keywords

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