97351-14-9Relevant academic research and scientific papers
One-pot synthesis of polysubstituted pyrrolidines from aminonitriles
Meyer, Nino,Werner, Frank,Opatz, Till
, p. 945 - 956 (2005)
α-Aminonitriles with a mono- or unsubstituted amino group as well as α-(alkylideneamino)nitriles can be employed as easily accessible α-aminocarbanion equivalents. Their α-deprotonation yields stabilized carbanions, which undergo smooth 1,4-addition to α,β- unsaturated carbonyl compounds. The resulting δ-keto-α-aminonitriles can be reductively cyclized to form polysubstituted pyrrolidines. Georg Thieme Verlag Stuttgart.
Ruthenium-porphyrin-catalyzed diastereoselective intramolecular alkyl carbene insertion into C-H bonds of alkyl diazomethanes generated in situ from N-tosylhydrazones
Reddy, Annapureddy Rajasekar,Zhou, Cong-Ying,Guo, Zhen,Wei, Jinhu,Che, Chi-Ming
, p. 14175 - 14180 (2015/01/09)
With a ruthenium-porphyrin catalyst, alkyl diazomethanes generated in situ from N-tosylhydrazones efficiently underwent intramolecular C(sp3)-H insertion of an alkyl carbene to give substituted tetrahydrofurans and pyrrolidines in up to 99% yield and with up to 99:1 cis selectivity. The reaction displays good tolerance of many functionalities, and the procedure is simple without the need for slow addition with a syringe pump. From a synthetic point of view, the C-H insertion of N-tosylhydrazones can be viewed as reductive coupling between a C=O bond and a C-H bond to form a new C-C bond, since N-tosylhydrazones can be readily prepared from carbonyl compounds. This reaction was successfully applied in a concise synthesis of (-)-pseudoheliotridane.
