Regioselective Crossed Aldol Reactions under Mild Conditions via Synergistic Gold-Iron Catalysis.

ABSTRACT: A synergistic gold/iron catalytic system was developed for sequential alkyne hydration and vinyl gold addition to aldehydes or ketones. Fe(acac)₃ was identified as an essential co-catalyst in preventing vinyl gold protodeauration and facilitating nucleophilic additions. Effective C-C bond formation was achieved under mild conditions (r.t.) with excellent regioselectivity and high efficiency (1% [Au], up to 95% yields). Extending reaction scope to intramolecular fashion achieved successful macrocyclization (16-31 ring sizes) with excellent yields (up to 90%, gram-scale) without extended dilution (0.2 M), which highlighted the great potential of this new crossed-aldol strategy in challenging target molecule synthesis.

SUBMITTER: Yuan T 

PROVIDER: S-EPMC10798669 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature