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Synfacts 2023; 19(02): 0145
DOI: 10.1055/s-0042-1753226
Metals in Synthesis

Atroposelective Ring-Closing Metathesis of Stereo-dynamic Trienes to Access Chiral Binaphthalenes

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Emilio Acuña Bolomey
Jončev Z, Sparr C. * University of Basel, Switzerland
Atroposelective Arene-Forming Alkene Metathesis.

Angew. Chem. Int. Ed. 2022;
61: e202211168
DOI: 10.1002/anie.202211168
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Key words

alkene metathesis - atropisomerism - binaphthalenes - molybdenum catalysis

Significance

An atroposelective molybdenum-catalyzed alkene metathesis under arene formation is disclosed. This reaction converts fluxional triene substrates into binaphthalene atropisomers with high enantioselectivities.


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Comment

In contrast to classical ring-closing metathesis, the aromatization of the triene substrate is an irreversible process. The methoxy substituent as a coordinating group proved to be crucial for the high enantioselectivity.


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Publication History

Article published online:
17 January 2023

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