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. Author manuscript; available in PMC: 2020 May 29.
Published in final edited form as: J Am Chem Soc. 2019 May 16;141(21):8557–8573. doi: 10.1021/jacs.9b02443

Scheme 7.

Scope of iron-catalyzed, diastereoselective [4+4]-cyclodimerization of 4-substituted dienes.a

Scheme 7

a Unless indicated otherwise, reactions were run on 0.5 mmol scale with 5 mol% [Fe] precatalyst. Values describe combined isolated yield of isomeric products, the portion of this isolated mixture comprised of [4+4]-cycloadducts as determined by gas chromatographic analysis, and the diastereomer ratio of the [4+4]-cycloadducts as determined by relative integration of diagnostic resonances in the quantitative 13C NMR spectrum of the isolated material. TBDPS = tert-butyldiphenylsilyl b with 2.5 mol% [Fe] on 5 mmol scale c with 5 mol% (iPrPI)Fe(MviMvi) d at 40 °C e 28% [4+2]