Regio- and Stereoselective α-Allylation with Enolates Prepared from N-C Axially Chiral Thiolactam and Lactam
Tatsunori Sakagami1, Ryosuke Matsui1, Shohei Aoyama1
1Department of Applied Chemistry, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
Abstract:
The reaction of allyl bromide derivatives with the enolate prepared from enantioenriched N-C axially chiral N-(2,5-di-tert-butylphenyl)-3,4-dihydroquinolin-2-one (lactam) and -thione (thiolactam) proceeded in a completely regio- and stereoselective manner to afford SN2 and SN2'-like products, respectively. Furthermore, through the conversion of thiolactam to lactam, the regiodivergent and stereoselective synthesis of N-C axially chiral lactams bearing a chiral tertiary α-carbon was achieved.
Related Concept Videos
α-Alkylation of Ketones via Enolate Ions
Regioselective Formation of Enolates
Stereochemical Effects of Enolization
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...


