PADAM reactions of α-aminoaldehydes: Identity of major and minor diastereomers from the Passerini reaction

The 100 facets of the Passerini reaction

“…Recently, the major stereoisomers have been recognized as syn . 35 The moderate stereoselection is obviously not a problem if the desired final products are α-ketoamides 50, derived by the oxidation of 49.…”

Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction

“…Recently, some examples of diastereoselective Passerini reactions on chiral enantiopure aldehydes or ketones have been reported, [11][12][13][14][15][16] but the related Ugi reaction is more problematic, not only because of the low diastereoselectivity typically achieved, but also for the easy racemization of aldehydes with astereogenic centres. 17 Better results have been accomplished with the so called Ugi-Joullié reaction.…”

Cyanoamidine Cyclization Approach to Remdesivir’s Nucleobase

“…18 Alternatively, Boc-protected aminopyrrole 9 could be utilized, which is notable since it is easily accessible in a single high-yielding step from 15 . 14b , 14f , 19 , 20 Treatment of 9 with acetic anhydride in formic acid 21 at room temperature gave formamide 12 in 70% yield.…”

“…In the first, 1-aminopyrrole ( 13 ), which can be prepared in two steps from 2,5-dimethoxyfuran ( 15 ), underwent formylation to provide 12 . Alternatively, Boc-protected aminopyrrole 9 could be utilized, which is notable since it is easily accessible in a single high-yielding step from 15 . ,,, Treatment of 9 with acetic anhydride in formic acid at room temperature gave formamide 12 in 70% yield.…”