Catalytic Enantioselective Synthesis of α‐(Benzylamino)cyclobutanones. Issue 20 (2nd June 2015)

• Record Type: Journal Article
• Authors: Melis, Nicola; Ghisu, Lorenza; Guillot, Régis; Caboni, Pierluigi; Secci, Francesco; Aitken, David J.; Frongia, Angelo
• Is Part Of: European journal of organic chemistry. Issue 20(2015)
• Page Start: 4358
• Page End: 4366
• Publication Date: 2015-06-02
• Subjects: Synthetic methods -- Organo­catalysis -- Enantioselectivity -- Amines -- Carbocycles -- Tautomerism; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500460
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An organocatalytic enantioselective synthesis of α‐(benzylamino)cyclobutanones has been achieved by employing a tandem condensation/intramolecular rearrangement/proton transfer reaction and starting from racemic α‐hydroxycyclobutanone and a selection of benzylamines. This reaction sequence afforded the products in good to high yields with moderate to high enantioselectivities. Abstract : An organocatalytic enantioselective synthesis of α‐(benzylamino)cyclobutanones has been achieved by employing a tandem condensation/intramolecular rearrangement/proton transfer reaction. The reaction sequence began from readily available racemic α‐hydroxycyclobutanone and a variety of benzylamines to afford the products in good to high yields and with moderate to high stereoselectivities.