Poly(isoprenecarboxylates) from Glucose via Anhydromevalonolactone.

A short and efficient synthesis of a series of isoprenecarboxylic acid esters (ICAEs) and their corresponding polymers is presented. The base-catalyzed eliminative ring-opening of anhydromevalonolactone () provides isoprenecarboxylic acid (), which was further transformed to the ICAEs. Reversible addition-fragmentation chain-transfer (RAFT) polymerization was used to synthesize high molecular weight (>100 kg mol) poly(isoprenecarboxylates) with dispersities () of ca.

Catalytic enantioselective carboannulation with allylsilanes.

The first catalytic asymmetric carboannulation with allylsilanes is presented. The enantioselective [3+2] annulation is catalyzed using a scandium(III)/indapybox complex with tetrakis-[3,5-bis(trifluoromethyl)phenyl]-borate (BArF) to enhance catalytic activity and control stereoselectivity. Functionalized cyclopentanes containing a quaternary carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high stereoselectivity.

Strategies for the enantioselective synthesis of spirooxindoles.

Oxindoles and spirooxindoles are important synthetic targets that are often considered to be prevalidated with respect to their biological activity and applications for pharmaceutical lead discovery. This review features efficient strategies for the enantioselective synthesis of spirocyclic oxindoles, focusing on reports in 2010 and 2011. Although enantioselective synthesis remains an ongoing challenge, exciting recent advances in this area feature spirooxindoles with greater complexity, up to eight stereogenic centers, more practical synthetic methods, and new catalytic activation strategies.