141246-72-2Relevant academic research and scientific papers
CONFORMATIONAL PREFERENCE IN BENZYLOXY- AND SILOXY-SUBSTITUTED THIANES, THIANE 1-OXIDES, AND THIANE 1,1-DIOXIDES
Nagao, Yoshimitsu,Goto, Michimasa,Kida, Kiyoshi,Shiro, Motoo
, p. 419 - 424 (2007/10/02)
Conformer ratios in 4-benzyloxy- and 4-siloxy-substituted thianes, cis- and trans-thiane-1-oxides, thiane 1,1-dioxides, and dihydrothiines were revealed on the basis of their low temperature 1H nmr analyses.Extreme benzyloxy- and siloxy-axial (or -pseudoa
Application of Homochiral Lithium Amide Base Chemistry to a Thiane Oxide System
Armer, Richard,Begley, Michael J.,Cox, Paul J.,Persad, Andrew,Simpkins, Nigel S.
, p. 3099 - 3104 (2007/10/02)
Treatment of the thiane oxide 6 with a homochiral lithium amide (HCLA) base 7, followed by electrophilic quench of the so-formed sulfoxide carbanion with Me3SiCl, MeI or t-BuCO2Et, gives the optically active products (+)-8, (+)-11 and (+)-12, respectively, in 55-60percent enantiomeric excess (ee).The reaction of 6 with the HCLA base 9 can be carried out in the presence of Me3SiCl (in situ quench conditions), in which case a silylation-in situ kinetic resolution process occurs, furnishing (-)-8 in low chemical yield, in up to 69percent ee.Further transformations of thiane oxides (+)-8 and (+)-11 involving reduction or removal of the ring sulfur atom were conducted, in order to establish the absolute configuration of the products.Hifhly stereoselective reduction of the keto sulfoxide (+)-12 was also carried out leading ultimately to an epoxide product 20 via opening of the thiane ring.
