Straightforward synthesis of chiral non-racemic α-boryl isocyanides

Abstract

A straightforward concise synthesis of chiral non-racemic aliphatic α-boryl isocyanides, relay intermediates for boron-based bioactive molecules by using multicomponent reaction, is presented. The short synthetic sequence comprises as key steps...

Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions

“…Synthesized following a reported literature procedure for dehydration of formylated compounds [ 36 ]: Under nitrogen, to a 0 °C solution of 2 (0.325 mmol, 1 eq) in dichloromethane (3.5 mL, 0.1 M), freshly distilled triethylamine (1.625 mmol, 5 eq) and phosphorus oxychloride (0.488 mmol, 1.5 eq) were added dropwise and the reaction stirred for 1.5 h at 0 °C. Aqueous NaHCO 3 sat.…”

“…Their potential was fully demonstrated in U-4CRs, allowing the identification of new bioactive inhibitors of human caseinolytic protease P (hClpP) [35]. Quite recently, similar α-boryl isocyanides are also reported in enantiopure form [36]. In general, stability of such compounds is likely guaranteed through tetracoordination at the boron atom, by means of the MIDA (N-methyliminodiacetyl) protecting group.…”