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Catalyst control over sixfold stereogenicity
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4634996
Author(s) Wu, Xingxing; Witzig, Reto; Beaud, Rodolphe; Fischer, Christian; Häussinger, Daniel; Sparr, Christof
Author(s) at UniBasel Sparr, Christof
Häussinger, Daniel
Year 2021
Title Catalyst control over sixfold stereogenicity
Journal Nature Catalysis
Volume 4
Number 6
Pages / Article-Number 457-462
Abstract Achieving control over higher-order stereogenicity is a long-standing goal in stereoselective catalysis to deliberately address more than a twofold number of stereoisomers per stereogenic unit. Current methods allow control over 2 " stereoisomers and their configurations are routinely assigned using the descriptors (R) and (S) or related binary codes. In contrast, conformational analysis extends beyond this dualistic treatment of stereoisomerism, which constitutes an unmet challenge for catalyst stereocontrol. Here, we report that sixfold stereogenicity is tractable by stereoselective catalysis. By controlling a configurationally stable stereogenic axis with six large rotational barriers, a catalytic [2 + 2 + 2] cyclotrimerization selectively governs the formation of one of six stereoisomers with up to 0:0:2:98:0:0 stereocontrol. Moreover, the stereoselectivity is redirectable by stereodivergent catalysis, providing four of the six stereoisomers as major stereoisomers. The underpinnings of conformational analysis and stereoselective catalysis are thereby conceptually reunited. Novel molecular architectures featuring distinct chemical topologies and unexplored chemical designs are anticipated from catalyst control over higher-order stereogenicity.
Publisher Springer Nature
ISSN/ISBN 2520-1158
edoc-URL https://edoc.unibas.ch/85735/
Full Text on edoc No
Digital Object Identifier DOI 10.1038/s41929-021-00615-z
ISI-Number 000655570300001
Document type (ISI) Article
 
   

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