1,2-Disubstituted Planar Chiral Ferrocene Derivatives from Sulfonamide-Directed ortho-Lithiation: Synthesis, Absolute Configuration, and Chiroptical Properties

Year: 2021

Authors: Ravutsov M., Dobrikov GM., Dangalov M., Nikolova R., Dimitrov V., Mazzeo G., Longhi G., Abbate S., Paoloni L., Fusi M., Barone V.

Autors Affiliation: Bulgarian Acad Sci, Ctr Phytochem, Inst Organ Chem, Sofia 1113, Bulgaria; Bulgarian Acad Sci, Inst Mineral & Crystallog Acad Ivan Kostov, Sofia 1113, Bulgaria; Univ Brescia, Dipartimento Med Mol & Traslaz, I-25123 Brescia, Italy; CNR, Ist Nazl Ott INO, Res Unit Brescia, I-25123 Brescia, Italy; Scuola Normale Super Pisa, I-56126 Pisa, Italy.

Abstract: A straightforward approach to the synthesis of a series of 1,2-disubstituted planar chiral ferrocenes was achieved using the ortho-directed lithiation of chiral ferrocenesulfonamides followed by a reaction with electrophilic reactants. The planar 1,2-functionalized ferrocenesulfonamides were obtained in good yields, and the individual diastereoisomers could be isolated in the pure form. The relative configurations of the chemical groups in positions 1 and 2, which are relevant for the planar chirality, were derived from NMR experiments, and the absolute configuration was determined by X-ray crystallography. Experimental ECD and VCD spectra were recorded, assigned, and interpreted by means of state-of-the-art quantum chemical computations, which allow for an unbiased analysis of the different structural factors that tune the overall spectroscopic features.

Journal/Review: ORGANOMETALLICS

Volume: 40 (5)      Pages from: 578  to: 590

More Information: This work has been supported by MIUR (Grant N.2017A4XRCA). The support by the Operational Program Science and Education for Smart Growth 2014-2020, cofinanced by the EU (Grant BG05M2OP001-1.002-0012) is gratefully acknowledged. This work was partially supported by the Bulgarian Ministry of Education and Science under the National Research Programme Young scientists and postdoctoral students approved by DCM no. 577/17.08.2018 and the program for the career development of young scientists, BAS (DFNP-132).
KeyWords: Circular-dichroism; Metal-complexes; Probe
DOI: 10.1021/acs.organomet.0c00712

Citations: 11
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