Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones
|Title:||Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones||Authors:||Baumann, Marcus; Baxendale, 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:||Cyclopentanone; Aza-Michael reaction; Baylis-Hillman reaction; Diastereoselectivity; H-bonding; Green 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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