Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones

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Title: Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones
Authors: Baumann, MarcusBaxendale, Ian R.
Permanent link: http://hdl.handle.net/10197/12608
Date: 15-Feb-2018
Online since: 2021-11-09T16:15:55Z
Abstract: An efficient entry into highly substituted cyclopentanones is presented based on functionalizing cyclopentenones by means of an aza-Michael reaction with different aniline nucleophiles. The excellent diastereoselectivity of this process is ascribed to H-bonding between a tertiary alcohol and the incoming nucleophiles. Additionally, the functionalization of the parent cyclopentenones via the Baylis-Hillman reaction is demonstrated. Together, these transformations showcase the elaboration of a simple precursor by installation of versatile functionalities at either the α- or β-position of the embedded enone and thus represent valuable methods for the construction of diversely functionalized cyclopentanones.
Funding Details: Royal Society
Type of material: Journal Article
Publisher: Georg Thieme
Journal: Synthesis
Volume: 50
Issue: 4
Start page: 753
End page: 759
Copyright (published version): 2018 Georg Thieme
Keywords: CyclopentanoneAza-Michael reactionBaylis-Hillman reactionDiastereoselectivityH-bondingGreen chemistry
DOI: 10.1055/s-0036-1591745
Language: en
Status of Item: Peer reviewed
ISSN: 0039-7881
This item is made available under a Creative Commons License: https://creativecommons.org/licenses/by-nc-nd/3.0/ie/
Appears in Collections:Chemistry Research Collection

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