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2 article(s) from Kvíčala, Jaroslav

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

Viola Kolaříková,
Markéta Rybáčková,
Martin Svoboda and
Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

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Scheme 1: RCEYM with Ru and Mo catalysts.

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Scheme 2: Beneficial effect of ethene atmosphere.

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Scheme 3: Enantioselective dienyne metathesis [21].

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Scheme 4: Diastereoselective endiyne metathesis [31].

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Figure 1: Oxaenediynes considered for the study of desymmetrizing RCEYM.

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Scheme 5: Synthesis of hepta-1,6-diyn-4-ol (4a).

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Scheme 6: Protection of hepta-1,6-diyn-4-ol (4a).

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Scheme 7: Alkylation of the protected diynols 7a and 8a.

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Scheme 8: Deprotection of protected diynols 7b, 7c and 8b–d.

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Scheme 9: Synthesis of the oxaenediynes 2 and 9 bearing an allyl or a methallyl group.

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Scheme 10: Synthesis of oxaenediynes 2e and 2f bearing ester or silyl groups.

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Scheme 11: Synthesis of alkadiynyl acrylates 10 and methacrylates 11.

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Figure 2: The ruthenium precatalysts employed.

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Scheme 12: RCEYM of oxaenediynes 2.

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Figure 3: Examples of side products of CM with ethene.

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Scheme 13: Attempted RCEYM of oxaenediynes 9, alkadiynyl acrylates 10 and methacrylates 11.

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Scheme 14: Diels–Alder reaction of dihydropyran 12b with N-phenylmaleimide (13).

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Figure 4: The four possible diastereoisomers of hexahydropyranoisoindole 14.

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Figure 5: Conformations of dihydropyran 12b.

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Figure 6: The two most stable s-trans (left) and s-cis (right) conformations of dihydropyran 12b.

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Figure 7: The two most stable transition states endo-trans 15B and exo-cis 15C (hydrogens are omitted for cla...

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Figure 8: PES of the Diels–Alder reaction of dihydropyran 12b and maleimide 13.

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Published 13 Nov 2020

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Computational study of productive and non-productive cycles in fluoroalkene metathesis

Markéta Rybáčková,
Jan Hošek,
Ondřej Šimůnek,
Viola Kolaříková and
Jaroslav Kvíčala

Beilstein J. Org. Chem. 2015, 11, 2150–2157, doi:10.3762/bjoc.11.232

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Scheme 1: Initiation, productive and non-productive cycles in alkene homometathesis.

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Figure 1: Initiation phase of the reaction of HG2 with ethene (1) and 1,1-difluoroethene (2).

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Figure 2: Initiation phase of the reaction of HG2 with ethene (1) and 1-fluoroethene (3).

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Figure 3: First part A of the catalytic cycle of homometathesis of 1,1-difluoroethene (2).

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Figure 4: Computed structures of complexes s2j and a2j.

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Figure 5: Second part B of the catalytic cycle of homometathesis of 1,1-difluoroethene (2).

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Figure 6: First part A of the catalytic cycle of homometathesis of 1-fluoroethene (3).

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Figure 7: Second part B of the catalytic cycle of homometathesis of 1-fluoroethene (3).

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Figure 8: Non-productive catalytic cycle of homometathesis of tetrafluoroethene (4).

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Figure 9: First part A of the catalytic cycle of homometathesis of chlorotrifluoroethene (5).

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Figure 10: Second part B of the catalytic cycle of homometathesis of chlorotrifluoroethene (5).

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Published 10 Nov 2015

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