Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones

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 inc...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 50; no. 4; pp. 753 - 759
Main Authors Baumann, Marcus, Baxendale, Ian R.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 15.02.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
aza-Michael reaction
diastereoselectivity
cyclopentanone
Baylis-Hillman reaction
H-bonding
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Summary: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 - or -position of the embedded enone and thus represent valuable methods for the construction of diversely functionalized cyclopentanones.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1591745