Conformationally Interlocked Amides: Remote Asymmetric Induction by Mechanical Transfer of Stereochemical Information
1998; Elsevier BV; Volume: 39; Issue: 1-2 Linguagem: Inglês
10.1016/s0040-4039(97)10443-9
ISSN1873-3581
AutoresJonathan Clayden, Jennifer H. Pink, Samreen A. Yasin,
Tópico(s)Axial and Atropisomeric Chirality Synthesis
ResumoThe axial conformation of an aromatic tertiary amide group may be powerfully influenced by an adjacent stereogenic centre. Because the amide axis can also control the formation of new chiral centres, the amide can act as a "relay centre" for the transmission of stereochemical information. Conformational interlocking of adjacent amide groups on an aromatic ring means that a pair of amide groups can be used in series to mediate asymmetric induction between remote stereogenic centres, for example those lying para across an aromatic ring. © 1997 Elsevier Science Ltd. All rights reserved.
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