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DOI: 10.1055/s-0036-1591745
Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones
We gratefully acknowledge funding by the Royal Society (M.B. and I.R.B.).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-bondingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591745.
- Supporting Information
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