Support groups: Phosphonium salts can be used as solubility‐control groups (SCGs) in small‐molecule and peptide synthesis (see scheme). The concept, which is a hybrid approach between solution‐ and solid‐phase syntheses, is illustrated by the preparation of 2‐substituted piperidine derivatives and a variety of small peptides with high yields and purities. In some cases, recycling of the support is possible.

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An efficient scalable route to synthesize the enantiomerically pure tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate is described. Compared to the original routes, significant improvements were made by using an innovative approach starting from commercially available chiral lactone. In this approach, one of the key steps described is an elegant epimerization/hydrolysis of the undesired diastereoisomer avoiding tedious purification. The chemistry has been scaled up to produce kilogram amounts of tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3azabicyclo[4.1.0]heptane-3-carboxylate in 43% yield over nine chemical transformations.