A short approach to trisubstituted γ-butyrolactones

Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon–Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates

“…Moreover, the acidic proton on the vinyldiazaphosphonate led to the following useful transformations such as alkylation 3k (70%) and isomerization 4d (>99%). Finally, in an attempt to functionalize the vinyl group of 3a to a diol derivative, we demonstrated a tandem dihydroxylation/lactonization of 3a to afford a diazaphosphono lactone 4e .…”

Highly Recyclable Chemo‐/Biocatalyzed Cascade Reactions with Ionic Liquids: One‐Pot Synthesis of Chiral Biaryl Alcohols

“…Our approach started with an asymmetric aldol addition of the titanium enolate derived from N ‐propionyloxazolidinone ( R )‐ 4 to acrolein to give aldol adduct 5 (87 % yield, dr > 95:5; Scheme ) 14–16. Protection of the secondary alcohol as its TBS ether cleanly provided aldol 6 in 93 % yield, which was smoothly converted into lactones 9 and 10 in 70 % yield and with more than 95:5 diastereoselectivity on treatment with 4‐methylmorpholine N ‐oxide (NMO) and catalytic amounts of OsO 4 in acetone/H 2 O at 0 °C (Scheme ) 17,18…”

Synthesis of the Macrolactone of Migrastatin and Analogues with Potent Cell‐Migration Inhibitory Activity

“…[14][15][16] Protection of the secondary alcohol as its TBS ether cleanly provided aldol 6 in 93 % yield, which was smoothly converted into lactones 9 and 10 in 70 % yield and with more than 95:5 diastereoselectivity on treatment with 4-methylmorpholine N-oxide (NMO) and catalytic amounts of OsO 4 in acetone/H 2 O at 0°C (Scheme 1). [17,18] At room temperature this process led to the formation of a mixture of lactones 9 and 10 in 77 % yield with 74:26 diastereoselectivity. These lactones were readily separated by flash column chromatography, and the oxazolidinone chiral auxiliary was recovered by crystallization from the reaction mixture.…”