Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones

Baumann, Marcus; Baxendale, Ian R

doi:10.1055/s-0036-1591745

Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones

Baumann, Marcus; Baxendale, Ian R

Authors

Marcus Baumann

Professor Ian Baxendale i.r.baxendale@durham.ac.uk
Professor

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.

Citation

Baumann, M., & Baxendale, I. R. (2018). Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones. Synthesis: Journal of Synthetic Organic Chemistry, 50(04), 753-759. https://doi.org/10.1055/s-0036-1591745

Journal Article Type	Article
Acceptance Date	Dec 1, 2017
Online Publication Date	Dec 21, 2017
Publication Date	Feb 1, 2018
Deposit Date	Feb 5, 2018
Publicly Available Date	Dec 21, 2018
Journal	Synthesis : journal of synthetic organic chemistry.
Print ISSN	0039-7881
Electronic ISSN	1437-210X
Publisher	Thieme Gruppe
Peer Reviewed	Peer Reviewed
Volume	50
Issue	04
Pages	753-759
DOI	https://doi.org/10.1055/s-0036-1591745