56819-81-9Relevant articles and documents
The versatility of α-chloropropargyl phenyl sulfide affords high stereo- and regioselectivities in indium-promoted coupling reactions under mild conditions
Mitzel, Thomas M.,Palomo, Carolyn,Jendza, Keith
, p. 136 - 145 (2007/10/03)
Coupling reactions between α-chloropropargyl phenyl sulfide (11) and a series of aldehydes under aqueous conditions are reported. Not only is good stereoselectivity observed between syn and anti isomeric products, but excellent regioselectivity is also witnessed. In reactions using indium metal as a promoter, the propargyl functionality (12) is retained, unlike the use of more traditional metals that result in formation of products containing a mixture of both propargyl (12) and allene (13) moieties. The reaction is postulated to proceed via either a chelated or nonchelated route, controlled by the presence or absence of indium (111) chloride, and may be used to create synthetically useful building blocks. The formation of epoxyalkyne (14) molecules, which are found in many natural products and have wide use as synthetic templates, is presented as one example.
Reaction of (α-Thioalkyl)chromium Compounds Prepared by Chromium(II) Reduction of α-Halo Sulfides
Nakatsukasa, Shigeki,Takai, Kazuhiko,Utimoto, Kiitiro
, p. 5045 - 5046 (2007/10/02)
Reduction of α-chloroalkyl phenyl (or methyl) sulfides with chromium(II) chloride in THF proceeds smoothly in the presence of LiI.The resulting (α-thioalkyl)chromium reagents add to aldehydes in a chemo- and stereoselective manner.
Asymmetric Sulfenylation of Tin(II) Enolates of Ketones and 3-Acyl-2-oxazolidones. Application to the Synthesis of Optically Active Epoxides
Yura, Takeshi,Iwasawa, Nobuharu,Clark, Richard,Mukaiyama, Teruaki
, p. 1809 - 1812 (2007/10/02)
In the presence of chiral diamines, the reaction between tin(II) enolates of ketones or 3-acyl-2-oxazolidones and thiosulfonates proceeds smoothly to give the corresponding β-keto sulfides with high enetioselectivity.Further, optically active epoxides are prepared from these β-keto sulfides.