Asymmetric Kulinkovich Hydroxycyclopropanation of Alkenes Mediated by Titanium(IV) TADDOLate Complexes

Marharyta Iskryk; Maryia Barysevich; Maksim Ošeka; Jasper Adamson; Dzmitry Kananovich

doi:10.1055/s-0037-1611709

Synthesis, Table of Contents

Synthesis 2019; 51(09): 1935-1948
DOI: 10.1055/s-0037-1611709

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Asymmetric Kulinkovich Hydroxycyclopropanation of Alkenes Mediated by Titanium(IV) TADDOLate Complexes

Marharyta Iskryk

^aTallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia Email: dzmitry.kananovich@taltech.ee

^bLaboratory of Steroids, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich 5/2, 220141 Minsk, Belarus

,

Maryia Barysevich

^aTallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia Email: dzmitry.kananovich@taltech.ee

^bLaboratory of Steroids, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich 5/2, 220141 Minsk, Belarus

,

Maksim Ošeka

^aTallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia Email: dzmitry.kananovich@taltech.ee

,

Jasper Adamson

^cNational Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia

,

Dzmitry Kananovich *

^aTallinn University of Technology, School of Science, Department of Chemistry and Biotechnology, Akadeemia tee 15, 12618 Tallinn, Estonia Email: dzmitry.kananovich@taltech.ee

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Abstract

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Dedicated to Prof. Oleg Kulinkovich on the occasion of his 70^th birthday

Abstract

Asymmetric Kulinkovich cyclopropanation of carboxylic esters with prochiral alkenes is reported. The process is mediated by titanium(IV) (4R,5R)-TADDOLate complexes and affords correspondingly (Z)- or (E)-cyclopropanols with up to 84–87% ee in the event of intra- or intermolecular olefin ligand exchange in intermediate titanacyclopropane [titanium(II)-alkene] species. Configuration of the olefin double bond is preserved in the cyclopropane products, pointing out on total retention of configuration at Ti–C bond in the cyclopropane forming step. The results have been interpreted in the framework of ate complex mechanism, suggesting formation of pentacoordinated titanium ate species as a prerequisite of high enantiocontrol.

Key words

titanium - Kulinkovich reaction - cyclopropanation - esters - cyclopropanols - asymmetric synthesis - reaction mechanisms

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References

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