Catalytic Synthesis of γ-Lactams via Direct Annulations of Enals and N-Sulfonylimines
Top Cited Papers
- 9 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (14) , 3131-3134
- https://doi.org/10.1021/ol051234w
Abstract
Cinnamaldehydes and N-sulfonylimines undergo direct annulations to cis-disubstituted γ-lactams via the intermediacy of catalytically generated homoenolates. Critical to the success of this process was overcoming inhibition of the N-heterocyclic carbene catalyst by the electrophilic imines. The overall process proceeds with good yields and diastereoselectivites and requires no stoichiometric reagents or additives.Keywords
This publication has 8 references indexed in Scilit:
- Organocatalyzed Conjugate Umpolung of α,β‐Unsaturated Aldehydes for the Synthesis of γ‐ButyrolactonesAngewandte Chemie International Edition in English, 2004
- Convenient synthesis of a reactive ester homoenolateTetrahedron Letters, 1999
- The [3 + 2] Annulation of Allylsilanes and Chlorosulfonyl Isocyanate: Stereoselective Synthesis of 2-PyrrolidinonesThe Journal of Organic Chemistry, 1999
- Piracetam and other structurally related nootropicsBrain Research Reviews, 1994
- Metal HomoenolatesPublished by Elsevier ,1991
- Conjugate addition of organocopper reagents to n-tosylated α, β-unsaturated amidesTetrahedron Letters, 1985
- The Dendralenes—a Neglected Group of Highly Unsaturated HydrocarbonsAngewandte Chemie International Edition in English, 1984
- Diazoalkanes from hydrazone anions. Novel oxidation reactionJournal of the American Chemical Society, 1967