SmCpR2-mediated cross-coupling of allyl and propargyl ethers with ketoesters and a telescoped approach to complex cycloheptanols.
A highly regio- and diastereoselective cross-coupling of allyl/propargyl ethers and δ-ketoesters, mediated by SmCpR2reagents, delivers decorated δ-lactones. Screening of the Cp ligands on Sm(ii) was employed to achieve high regio and diastereocontrol in some cases. Crucially, SmI2gave unsatisfactory results in the transformation. The process has been exploited in a telescoped approach to complex cycloheptanols in which two Sm(ii) reagents act in turn on the simple starting materials.
School of Chemistry, The University of Manchester, Oxford Rd, Manchester, M13 9PL, UK. david.mills@manchester.ac.uk david.j.procter@manchester.ac.uk.
Mateusz P
MP
Plesniak
School of Chemistry, The University of Manchester, Oxford Rd, Manchester, M13 9PL, UK. david.mills@manchester.ac.uk david.j.procter@manchester.ac.uk.
Xavier
X
Just-Baringo
School of Chemistry, The University of Manchester, Oxford Rd, Manchester, M13 9PL, UK. david.mills@manchester.ac.uk david.j.procter@manchester.ac.uk.
Fabrizio
http://orcid.org/0000-0002-1743-8338
F
Ortu
School of Chemistry, The University of Manchester, Oxford Rd, Manchester, M13 9PL, UK. david.mills@manchester.ac.uk david.j.procter@manchester.ac.uk.
David P
DP
Mills
School of Chemistry, The University of Manchester, Oxford Rd, Manchester, M13 9PL, UK. david.mills@manchester.ac.uk david.j.procter@manchester.ac.uk.
David J
DJ
Procter