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Synthesis 2018; 50(04): 753-759
DOI: 10.1055/s-0036-1591745
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© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones

Marcus Baumann  *
a   Department of Chemistry, University of Durham, South Road, DH1 3LE, Durham, United Kingdom
b   UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland   Email: marcus.baumann@ucd.ie
,
Ian R. Baxendale
a   Department of Chemistry, University of Durham, South Road, DH1 3LE, Durham, United Kingdom
› Author AffiliationsWe gratefully acknowledge funding by the Royal Society (M.B. and I.R.B.).
Further Information

Publication History

Received: 30 October 2017

Accepted after revision: 01 December 2017

Publication Date:
21 December 2017 (online)

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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.

Key words

cyclopentanone - aza-Michael reaction - Baylis–Hillman reaction - diastereoselectivity - H-bonding

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591745.
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