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Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction

DOI: 10.1002/ejoc.201700193 DOI Help

Authors: Kaiheng Zhang (University of Southampton) , Marta Meazza (University of Southampton) , Vojtěch Dočekal (Charles University in Prague) , Mark Light (University of Southampton) , Jan Veselý (Charles University in Prague) , Ramon Rios (University of Southampton)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: European Journal Of Organic Chemistry , VOL 2017 , PAGES 1749 - 1756

State: Published (Approved)
Published: April 2017
Diamond Proposal Number(s): 8521

Abstract: An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee).

Journal Keywords: Spiro lactams; Organocatalysis; Asymmetric synthesis; Michael addition; Enantioselective

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction