Efficient Isocyanide-less Isocyanide-Based Multicomponent Reactions

Abstract

Isocyanides are the “Jekyll and Hyde” of organic chemistry allowing for extremely interesting transformations that are not only extremely odorous but also noxious. Therefore, an isocyanide-less isocyanide-based multicomponent reaction (IMCR) has been developed, and this protocol is expected to replace many of the old procedures in the future not only in IMCR but in other areas of organic chemistry as well.

Enantiospecific Total Syntheses of (+)‐Hapalindole H and (−)‐12‐epi‐Hapalindole U

“…Oxidation of the secondary alcohol by IBX in CH 3 CN under reflux condition afforded corresponding ketone 15 in 88 % yield. Microwave aided reductive amination of ketone 15 at 180 °C for 3 min followed by subsequent dehydration by the Burgess reagent furnished 1 and 13 in 2:7 diastereomeric ratio. Formation of diastereomers, 1 and 13 , in an uneven ratio can be rationalized by selective equatorial attack of the hydride ion onto the iminium ion during reductive amination step.…”

Expansion of chemical space for collaborative lead generation and drug discovery: the European Lead Factory Perspective

“…Indeed, a significant number of unprecedented spiro, bridged, and fused polycycles with different degrees of saturation, conjugation, and substitution have been synthesized and expanded to a library format. This has been recently exemplified by several publications from the ELF chemistry groups detailing the associated design and validation aspects [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]. Given that most theoretical ring systems remains unexplored [39], the synthesis of novel rings represents one of the strategies embraced by the ELF chemistry consortium to expand the available chemical space.…”

Structure and Reactivity of Glycosyl Isocyanides

“…In addition, we demonstrate our synthetic strategy to access different glycoconjugate scaffolds. Based on our recently disclosed Leuckart‐Wallach (LW) approach, , with some experimental improvements (reducing the refluxing temperature from 140 °C to 100 °C, increased dramatically the yield), we performed the regio‐ and stereospecifically the reductive amination on the 1‐OH‐unprotected sugars 1 , affording the corresponding glucosyl ( 2 ), galactosyl ( 3 ), arabinosyl ( 4 ), ribosyl ( 5 ), lactosyl ( 6 ) and maltotriosyl ( 7 ) formamides in good yields. Since we were primarily interested in the structural information, we also resynthesized the glucosyl and arabinosyl formamides.…”