5070-90-6Relevant articles and documents
Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates
Górski, Bartosz,Basiak, Dariusz,Grzesiński, ?ukasz,Barbasiewicz, Micha?
supporting information, p. 7660 - 7663 (2019/08/30)
The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin-Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.
Iterative synthesis of alkenes by insertion of lithiated epoxides into boronic esters
Bojaryn, Kevin,Fritsch, Stefan,Hirschhaüser, Christoph
supporting information, p. 2218 - 2222 (2019/04/10)
The insertion of lithiated epoxides into boronic esters followed by thermal syn-elimination provides a stereospecific entry to alkenes. This process avoids transition metals and is amenable to iteration to provide higher substitution patterns.
Stereoselective Synthesis of Unhindered Olefins by 2-Fold Extrusion Reactions
Collazo, Luis R.,Guziec, Frank S.
, p. 43 - 46 (2007/10/02)
Two-fold extrusion reactions of 1,3,4-thiadiazolines 1 provide a convenient stereoselective route to unhindered Z-olefins.An improved preparation of the thiadiazolines involves reaction of an aldehyde with H2S-hydrazine, followed by in situ oxidation of the intermediate predominantly trans thiadiazolidine 2.Stereospecific extrusion of nitrogen yields the cis-thiirane which upon treatment with triphenylphosphine affords the corresponding Z-alkene in good yields.