A General Access to 2-Silylthiazolidines and Their Reactions Under Fluoride Ion Conditions

Abstract

2-Trimethylsilylthiazolidines were readily obtained through reaction of aminoethanethiol with (bromomethoxymethyl)trimethylsilane and efficiently N-functionalized with a variety of protecting groups. Such N-protected thiazolidines can then be satisfactorily reacted with several organic electrophiles under fluoride ion conditions, with a clean transfer of the thiazolidine moiety, to afford good yields of 2functionalized heterocycles.

Synthesis and Stereoselective Functionalization of Sulfur-Containing Silyl Heterocycles

“…In fact, in that case, under the same experimental conditions, a clean cyclization to oxazolidinones 12 and 13 was observed (Scheme 6). 13 The versatility of the present methodology is further illustrated by another example. When the protecting group itself contains an Downloaded by [University of Chicago Library] at 12:45 26 December 2014 SCHEME 6 electrophilic center, a clean cyclization occurs, leading in good yields to policyclic compounds.…”

Synthesis and stereoselective functionalization of silylated heterocycles as a new class of formyl anion equivalents

“…The thiazolidine thus obtained can, again in situ, be easily protected at the nitrogen atom with different groups, such as mesyl, tosyl, acetyl, benzoyl, cinnamoyl, BOC and Cbz, to afford a general route to various N-functionalized 2-silylthiazolidines 24 through a simple one-pot procedure (Table 7). 83 Reaction of the so-obtained silyl thiazolidines with aldehydes under fluoride catalysis uncovered an efficient methodology for their functionalization (Table 8), showing a consistency with different protecting groups on the endocyclic nitrogen, and occurring smoothly in the presence of different N-protecting moieties such as tosyl, mesyl, acetyl and BOC. No reaction was observed when the protecting groups were benzoyl and cinnamoyl, with only the desilylated thiazolidine being recovered from the reaction mixture in these instances.…”

Synthesis of A New Class of Sulfurated and Selenated Silyl Heterocycles

“…Our interest in the chemistry of both sulfur and silicon containing molecules led us to disclose a novel methodology for the synthesis and functionalization of 2-silyl five-membered sulfurated heterocycles. 1 We found that a convenient way to access such molecules was through the reaction of bromo(methoxy)methyl trimethylsilane with 1,2-dithiols, β-mercaptoalcohols, and β-mercaptoamines leading to the formation of silylated 1,3-dithiolanes, 2 1,3-oxathiolanes, 3 and 1,3-thiazolidines, 4 respectively. Besides thiaheterocycles, the related seleno-containing analogues are also interesting compounds, generally characterized by a relevant bioactivity.…”