Reaction of allylic boron and aluminum "ate" complexes with organic halides and carbonyl compounds. Trialkylboranes as regio-, stereo-, and chemoselective control elements

A versatile kinetic alkylation-ozonolysis route for the synthesis of lactones: chiral γ-lactones and racemic δ-lactones

“…The 3-methyl-1,5-hexadien-3-ol (2.98g, 88%, 95% pure by GC) which distilled over 30min was collected in an ice/water cooled receiver. The spectroscopic data obtained for the product were consistent with published data 35 . (iv) Preparation of 6-hepten-2-one (5).…”

Palladium(0) versus Nickel(0) Catalysis in Selective Functional‐Group‐Tolerant sp3–sp3 Carbon–Carbon Bond Formations

“…The success of allyl boronate 3 in this Pd 0 -catalyzed nonsymmetrical sp 3 -sp 3 C-C coupling under these mild conditions is striking. [15,16] Indeed, allyl magnesium bromide, [8] allyl trimethylsilane, [10] or allyl trifluoroborate [17,18] provided, in our hands, under the same mild conditions after 16 h reaction time, only the corresponding 1,2-adduct, a complex mixture, or a trace amount of desired product, respectively.…”

Preparation and reactions of water stable hypervalent 10‐Sn‐5 allyl ate complexes

“…This stereoselectivity also provided evidence that the ate complex is the reacting species and not dissociated crotyl lithium, which is reckoned to give unselective product mixtures [1]. The use of less reactive aromatic aldehydes revealed that, although higher temperatures were required, stereoselectivity was retained to a high degree (entries 3-5) [20]. The use of LiF, which is a fluorine source, and LiBF 4 , which is a potential fluorine source, led to some decrease in the diastereomeric ratio (entries 6 and 7).…”

“…The crude mixture was then subjected to chromatographic treatment (SiO 2 , CH 2 Cl 2 ) to furnish the pure product. [20]. 1 …”