related to degree

• Kwok, Sen Wai, Ph.D. in Organic Chemistry, Scripps Research 2005 - 2011

authors

• Kwok, Sen Wai
• Zhang, L.
• Grimster, N. P.
• Fokin, Valery

publication date

• March 2014

journal

• Angewandte Chemie-International Edition  Journal

abstract

• A convenient one-pot asymmetric synthesis of 2,3-dihydropyrroles from in situ generated triflated triazoles and olefins is described that further expands the utility of azavinyl carbene chemistry and provides access to an important class of cyclic enamides. Mechanistic investigations support the involvement of triflated cyclopropylaldimine intermediates in the formation of 2,3-dihydropyrrole. To the best of our knowledge, this is the first example of a chiral Br?nsted acid catalyzed rearrangement of cyclopropylimines into enantioenriched 2,3-dihydropyrroles.
• A convenient one-pot asymmetric synthesis of 2,3-dihydropyrroles from in situ generated triflated triazoles and olefins is described that further expands the utility of azavinyl carbene chemistry and provides access to an important class of cyclic enamides. Mechanistic investigations support the involvement of triflated cyclopropylaldimine intermediates in the formation of 2,3-dihydropyrrole. To the best of our knowledge, this is the first example of a chiral Brønsted acid catalyzed rearrangement of cyclopropylimines into enantioenriched 2,3-dihydropyrroles.

subject areas

• Alkenes
• Catalysis
• Molecular Structure
• Rhodium
• Stereoisomerism
• Triazoles

keywords

• azavinyl carbenes
• dihydropyrroles
• enamides
• rhodium
• triazoles

PubMed Central ID

• PMC4082713

International Standard Serial Number (ISSN)

• 1433-7851

Digital Object Identifier (DOI)

• 10.1002/anie.201306706

PubMed ID

• 24677710

start page

• 3452

end page

• 3456

volume

• 53

issue

• 13