Oxovanadium(IV) Complex-mediated Catalysis in Mukaiyama-type Aldol Additions

Abstract

Condensation of vanadyl sulfate with 2,2'-biphenol in the presence of N-containing ligands provides oxovanadium(IV) complexes which serve as efficient catalysts in Mukaiyama aldol reactions to afford aldol products in 52-100% yields with diastereoselectivities of up to 90/10 (anti/syn)

Removal of Acid-Labile Protecting Groups on Carbohydrates Using Water-Tolerant and Recoverable Vanadyl Triflate Catalyst

“…The synthetic use of vanadium-containing complexes has been extensively investigated. They are utilized as reagents or catalysts for redox-type C−C bond formation , in the presence of suitable co-oxidants . Over the past years, many water-tolerant vanadyl and other oxometallic species have been developed as recoverable, amphoteric catalysis and used in nucleophilic acyl substitution, benzylidenation, and isopropylidenation .…”

Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes

“…11 By taking advantage of their electrophilic nature toward oxygen functionality, 12 we have recently unraveled the catalytic activity of 2,2′-biphenol-based vanadyl complexes toward Mukaiyama aldol additions. 13 A diastereoselectivity of up to 90/10 (anti/syn) was achieved in the preliminary study. As part of our continuing search for asymmetric variants of oxovanadium(IV) complexes along with the recent finding of Uang on the use of V(O)(acac) 2 in the aerobic oxidative coupling of 2-naphthols, 14 we focussed on developing a new type of tridentate chiral vanadyl complex specifically active for both the aldol and the coupling processes.…”

“…Oxovanadium(IV) complexes have been commonly utilized as precatalysts for olefin epoxidation and sulfide oxidation when combined with O 2 or peroxide co-oxidants we have recently unraveled the catalytic activity of 2,2‘-biphenol-based vanadyl complexes toward Mukaiyama aldol additions . A diastereoselectivity of up to 90/10 (anti/syn) was achieved in the preliminary study.…”