Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones

Baumann, Marcus; Baxendale, Ian R

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
• Public URL: https://durham-repository.worktribe.com/output/1339735