Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene

Allison P. Carley; Sally Dixon; Jeremy Dunbar Kilburn

doi:10.1055/s-0029-1216885

Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene

Allison P. Carley, Sally Dixon, Jeremy Dunbar Kilburn

University of Southampton

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

16 Citations (Scopus)

Abstract

A series of readily prepared bifunctional catalysts promote the Michael addition of cyclohexanone to trans-beta-nitrostyrene with excellent asymmetric induction. The enantioselection (up to 97%) and diastereoselection (up to 95:5) is comparable to other pyrrolidine-thiourea organocatalysts recently reported, however, reaction times are often shorter.

Original language	English
Pages (from-to)	2509-2516
Number of pages	8
Journal	Synthesis
Issue number	15
DOIs	https://doi.org/10.1055/s-0029-1216885
Publication status	Published - 3 Aug 2009

Keywords

addition reactions
asymmetric catalysis
Michael additions
bifunctional catalysis
nitroolefin
PRIMARY AMINE-THIOUREA
BIFUNCTIONAL ORGANOCATALYSTS
CONJUGATE ADDITION
NITRO-MICHAEL
PROTECTING GROUP
ALDOL REACTIONS
NITROOLEFINS
KETONES
PROLINE
DERIVATIVES

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title = "Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene",

abstract = "A series of readily prepared bifunctional catalysts promote the Michael addition of cyclohexanone to trans-beta-nitrostyrene with excellent asymmetric induction. The enantioselection (up to 97%) and diastereoselection (up to 95:5) is comparable to other pyrrolidine-thiourea organocatalysts recently reported, however, reaction times are often shorter.",

keywords = "addition reactions, asymmetric catalysis, Michael additions, bifunctional catalysis, nitroolefin, PRIMARY AMINE-THIOUREA, BIFUNCTIONAL ORGANOCATALYSTS, CONJUGATE ADDITION, NITRO-MICHAEL, PROTECTING GROUP, ALDOL REACTIONS, NITROOLEFINS, KETONES, PROLINE, DERIVATIVES",

author = "Carley, {Allison P.} and Sally Dixon and Kilburn, {Jeremy Dunbar}",

year = "2009",

month = aug,

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doi = "10.1055/s-0029-1216885",

language = "English",

pages = "2509--2516",

journal = "Synthesis",

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T1 - Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene

AU - Carley, Allison P.

AU - Dixon, Sally

AU - Kilburn, Jeremy Dunbar

PY - 2009/8/3

Y1 - 2009/8/3

N2 - A series of readily prepared bifunctional catalysts promote the Michael addition of cyclohexanone to trans-beta-nitrostyrene with excellent asymmetric induction. The enantioselection (up to 97%) and diastereoselection (up to 95:5) is comparable to other pyrrolidine-thiourea organocatalysts recently reported, however, reaction times are often shorter.

AB - A series of readily prepared bifunctional catalysts promote the Michael addition of cyclohexanone to trans-beta-nitrostyrene with excellent asymmetric induction. The enantioselection (up to 97%) and diastereoselection (up to 95:5) is comparable to other pyrrolidine-thiourea organocatalysts recently reported, however, reaction times are often shorter.

KW - addition reactions

KW - asymmetric catalysis

KW - Michael additions

KW - bifunctional catalysis

KW - nitroolefin

KW - PRIMARY AMINE-THIOUREA

KW - BIFUNCTIONAL ORGANOCATALYSTS

KW - CONJUGATE ADDITION

KW - NITRO-MICHAEL

KW - PROTECTING GROUP

KW - ALDOL REACTIONS

KW - NITROOLEFINS

KW - KETONES

KW - PROLINE

KW - DERIVATIVES

U2 - 10.1055/s-0029-1216885

DO - 10.1055/s-0029-1216885

M3 - Article

SN - 0039-7881

SP - 2509

EP - 2516

JO - Synthesis

JF - Synthesis

IS - 15

ER -

Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene

Abstract

Keywords

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