ABSTRACT
[reaction: see text] Diastereoselective reductive coupling reactions of omega-vinyl tethered cyclic imides are achieved by a preexisting stereocenter at an allylic position. Particularly noteworthy is the effective use of a 1:2 mixture of Ti(O-i-Pr)4 and n-BuLi to afford the N-acylhemiaminal products in good yields.
ABSTRACT
[reaction: see text]. Inter- and intramolecular titanium-mediated coupling reactions of N-acylpyrroles are reported for convenient functionalization of terminal olefins. Comparison with the Kulinkovich reaction of esters and other carboxylic acid derivatives is also included.
Subject(s)
Pyrroles/chemistry , Pyrroles/chemical synthesis , Titanium/chemistry , Alkenes/chemistry , Alkylation , Catalysis , Indicators and Reagents , Molecular StructureABSTRACT
[reaction: see text] Inter- and intramolecular titanium-mediated cyclopropanation reactions of vinylogous esters are reported. Comparison between the Kulinkovich cyclopropanation of esters and vinylogous esters provides mechanistic insight regarding reaction variables such as reaction temperature, solvents, and a Lewis acid additive.
