Intramolecular transfer of axial to central chirality in the strecker reaction. Synthesis and stereochemistry of 5,7-dicyano-6,7-dihydro-5H-dibenz[c,e]azepines
1999; Elsevier BV; Volume: 55; Issue: 25 Linguagem: Inglês
10.1016/s0040-4020(99)00399-3
ISSN1464-5416
AutoresM. Tichý, Miloš Buděšı́nský, Jana Günterová, Jiřı́ Závada, Jaroslav Podlaha, Ivana Cı́sařová,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe reaction of unsubstituted as well as 6,6′-disubstituted biphenyl-2,2′-dicarboxaldehydes with HCN and ammonia or methylamine has been investigated. It has been found that the final reaction step, the addition of HCN to the intermediary cyclic imino nitriles, is a strictly diastereoselective process, yielding always only one of the two diastereoisomers of the title products, the stereoselection being controlled by the chiral twist of the biaryl axis.
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