An efficient method for the synthesis of substituted TosMIC precursors

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

“…Tosylformamides 16 were prepared by simply heating the aldehyde, formamide, TMSCl and p-toluenesulfinic acid in a 1:1 mixture of toluene and acetonitrite at 50 C for 5 h in 70-93% yield. Dehydration of formamide 16 with POCl 3 in THF gave the isocyanides 7-13 in 68-78% yield [9].…”

“…Aryl-substituted TosMIC Sisko et al [9] have developed an improved procedure for the preparation of aryl-substituted tosylmethyl isocyanides. The TosMIC analogs 7-13 were prepared by Sisko et al (Figure 1).…”

Asymmetric Catalytic Phenyl Transfer to Imines: Highly Enantioselective Synthesis of Diarylmethylamines.

“…The fact that peralkylated anions such as 1 can be considered as being negatively charged ™alkane balls∫ is of particular relevance as there is considerable interest in the isolation and structure of metal±alkane complexes. [10] The structures of simple alkali-metal salts of Me 12 ] À have been reported, [11] while the maingroup-metal complex [nBu 3 Sn] ] is a closely associated ion-pair in the solid state, a structure that is thought to be retained in solution. [5] However, no analogous transition-metal complexes have been described.…”

“…This class of N-acylimine precursors is readily available in a one-pot synthesis from benzaldehyde, amide, and p-tolylsulfinic acid. [11] The addition to the imine then proceeds by deprotonation of amide 7 a, followed by elimination of the sulfinate to form N-formylimine 8 a. Addition of the zinc reagent gives rise to the N-formylamine 9 a.…”

3,5‐Dihydro‐2H‐thieno[2,3‐c]pyrrole 1,1‐Dioxide – A New Simple Pyrrole Unit. Preliminary Communication

“…To the best of our knowledge 3 is a new compound. Modifications introduced in the assembly, such as a-substituted TsMIC [39], 4-or 5-substituted 2-sulfolenes [38], would generate substituted b'-sulfolenopyrroles under similar reaction conditions.…”