Carbanions of 1,3‐Dithianes. Reagents for CC Bond Formation by Nucleophilic Displacement and Carbonyl Addition

Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis

“…Target molecule 1 may be derived from protected triol 2, in which the carbonyl group is masked as a dithiane. Compound 2 may be accessed via the assembly of two fragments 3 and 4 employing a dithiane coupling strategy (27)(28)(29)(30)(31). Both 3 and 4 are available from the ␣,␤-unsaturated thioesters 5 and 6 (11)(12)(13), each with a different alcohol protecting group to allow selective deprotection in later stages of the synthesis.…”

Investigations into the preparation of sila-β-diketones via 2-trimethylsilyl-1,3-dithianes: structural characterization of a second polymorph of bis(2,2,6,6-tetramethyl-2-sila-3,5-heptanedionato)copper(II)

“…As part of our investigations on the synthesis of sila-b-diketones, we report here on the utilization of this approach, combined with the umpolung afforded by 1,3-dithiane anions [12][13][14][15][16], to provide an alternative synthesis for 2,2,6,6-tetramethyl-2-silaheptane-3,5-dione (tmshdH; 2). The major byproduct of Journal of Organometallic Chemistry 689 (2004) 71-81 www.elsevier.com/locate/jorganchem this procedure, 2; 2 0 -bis(trimethylsilyl)-2; 2 0 -bi-1,3-dithiane (3), as well as a second polymorph of Cu(tmshd) 2 (4), were characterized by X-ray diffraction methods.…”

Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis

“…In 1965, Corey and Seebach introduced the use of 1,3-dithianes as important umpolung linchpins in organic synthesis [14,15]. For over 40 years, this approach has become a mainstay for the union of both simple and complex fragments [16][17][18][19].…”

“…For over 40 years, this approach has become a mainstay for the union of both simple and complex fragments [16][17][18][19]. Among the most important features of these compounds is their stability under both acidic and basic conditions [20,21] and their potential utility in organic synthesis as acyl carbanion equivalents in carbon-carbon bond forming reactions [14,20,21]. A wide range of electrophiles, including alkyl halides, aldehydes, and epoxides, react smoothly with the derived acylanion equivalents [20,21].…”