BJOC - A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

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A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

Kay M. Brummond and Joshua M. Osbourn

Beilstein J. Org. Chem. 2010, 6, No. 33. https://doi.org/10.3762/bjoc.6.33

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Brummond, K. M.; Osbourn, J. M. Beilstein J. Org. Chem. 2010, 6, No. 33. doi:10.3762/bjoc.6.33

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TY  - JOUR
A1  - Brummond, Kay M.
A1  - Osbourn, Joshua M.
T1  - A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
JF  - Beilstein Journal of Organic Chemistry
PY  - 2010///
VL  - 6
SP  - 33
SN  - 1860-5397
DO  - 10.3762/bjoc.6.33
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.6.33
KW  - allene
KW  - propargylic acetate
KW  - spirooxindole
KW  - thermal [2 + 2] cycloaddition
KW  - thermal [3,3]-sigmatropic rearrangement
KW  - vinylidene indolin-2-one
N2  - The synthesis of C3-carbocyclic spirooxindoles was realized by way of an intramolecular [2 + 2] cycloaddition reaction between a vinylidene indolin-2-one and an alkyne. The cycloaddition reaction occurs selectively with the distal double bond of the allene, is tolerant of a phenyl and trimethylsilyl group on the terminus of the alkyne, and can be used to access bicyclo[4.2.0]octadienes and bicyclo[5.2.0]nonadienes. The allene precursors are not observed, but are likely intermediates of an infrequently encountered thermal [3,3]-sigmatropic rearrangement of a propargylic acetate.
ER  -

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Scholarly Works

Dyachenko, V. D.; Baryshev, B. N.; Nenajdenko, V. G. [3,3]-Sigmatropic rearrangements: a variety of methods and recent advances. Russian Chemical Reviews 2022, 91, RCR5039. doi:10.1070/rcr5039
Roh, H. J.; Lim, J. W.; Ryu, J. Y.; Lee, J.; Kim, J. N. One-pot synthesis of 3-naphtho[2,1-b]furanyl-2-oxindoles from 3-(arylethynyl)-3-hydroxyindolin-2-ones and 2-naphthols. Tetrahedron Letters 2016, 57, 4280–4283. doi:10.1016/j.tetlet.2016.08.017
Snyder; Schaumann. Applications of Domino Transformations in Organic Synthesis 2 - 2.1.2 Domino Reactions Including [2 + 2], [3 + 2], or [5 + 2] Cycloadditions. Applications of Domino Transformations in Organic Synthesis 2; Georg Thieme Verlag KG, 2016. doi:10.1055/sos-sd-220-00038
Oh, C. H.; Kim, J. H.; Piao, L.; Yu, J.; Kim, S. Y. Gold Carbenes from Substituted Propargyl Acetates: Intramolecular Ene‐type Reactions to 2‐Acetoxynaphthalene Derivatives. Chemistry (Weinheim an der Bergstrasse, Germany) 2013, 19, 10501–10505. doi:10.1002/chem.201301384
Brummond, K. M.; Osbourn, J. M. Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles. Beilstein journal of organic chemistry 2011, 7, 601–605. doi:10.3762/bjoc.7.70
Fu, X.-P.; Liu, L.; Wang, D.; Chen, Y.-J.; Li, C.-J. “On water”-promoted direct alkynylation of isatins catalyzed by NHC–silver complexes for the efficient synthesis of 3-hydroxy-3-ethynylindolin-2-ones. Green Chemistry 2011, 13, 549–553. doi:10.1039/c0gc00807a

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