Transition-metal-free nucleophilic allylic substitutions of Morita–Baylis–Hillman bromides with aliphatic and aromatic amines

The present study reports the organocatalytic enantioselective allylic amination of Morita-Baylis-Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Brønsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.

show abstract

Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates

Dočekal

Šimek

Dračínský

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

show abstract

New Morita-Baylis-Hillman (MBH) phosphonium salts from alcohols to the synthesis of 2-alkenyl- and 2-alkylidenecyclohexenones

Elleuch

Msalbi

Mhasni³

et al. 2023

Journal of Molecular Structure

View full text Add to dashboard Cite

Transition metal-free direct nucleophilic α-substitution of Morita–Baylis–Hillman alcohols with amines and thiols

Oueslati

Baioui

Rezgui

2017

Synthetic Communications

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Transition-metal-free nucleophilic allylic substitutions of Morita–Baylis–Hillman bromides with aliphatic and aromatic amines

Cited by 3 publications

References 14 publications

Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates

Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates

New Morita-Baylis-Hillman (MBH) phosphonium salts from alcohols to the synthesis of 2-alkenyl- and 2-alkylidenecyclohexenones

Transition metal-free direct nucleophilic α-substitution of Morita–Baylis–Hillman alcohols with amines and thiols

Contact Info

Product

Resources

About