Organic Letters
Letter
Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-
Dihydrofurans. Org. Lett. 2017, 19, 3043−3046.
and Cation-Mediated Interaction of Its seco-Derivatives with G-
Quadruplexes. J. Am. Chem. Soc. 2011, 133, 1044−1051.
(12) Cheng, J.; Jiang, X.; Zhu, C.; Ma, S. Palladium-catalyzed three-
component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates,
organic halides, and amines: an effective protocol for the synthesis of
4,5-dihydro-1H-pyrrole derivatives. Adv. Synth. Catal. 2011, 353,
1676−1682.
(6) Ortega, A.; Manzano, R.; Uria, U.; Carrillo, L.; Reyes, E.; Tejero,
T.; Merino, P.; Vicario, J. L. Catalytic Enantioselective Cloke−Wilson
Rearrangement. Angew. Chem., Int. Ed. 2018, 57, 8225−8229; Angew.
Chem. 2018, 130, 8357−8361.
(7) Yadav, V. K.; Balamurugan, R. Silicon-Assisted Ring Opening of
Donor−Acceptor Substituted Cyclopropanes. An Expedient Entry to
Substituted Dihydrofurans. Org. Lett. 2001, 3, 2717−2719.
(8) (a) Bowman, R. K.; Johnson, J. S. Nickel-Catalyzed Rearrange-
ment of 1-Acyl-2-vinylcyclopropanes. A Mild Synthesis of Substituted
Dihydrofurans. Org. Lett. 2006, 8, 573−576. (b) Lin, C.-H.; Pursley,
D.; Klein, J. E. M. N.; Teske, J.; Allen, J. A.; Rami, F.; Koehn, A.;
Plietker, B. Non-decarbonylative photochemical versus thermal
activation of Bu4N[Fe(CO)3(NO)]the Fe-catalyzed Cloke−Wilson
rearrangement of vinyl and arylcyclopropanes. Chem. Sci. 2015, 6,
7034−7043.
(9) For important contributions related to our chemistry, see:
(a) Chaplin, D. A.; Fox, M. E.; Kroll, S. H. B. Dynamic kinetic
resolution of dehydrocoronamic acid. Chem. Commun. 2014, 50,
5858−5860. (b) Feng, J.-J.; Zhang, J. An Atom-Economic Synthesis of
Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Cata-
lyzed Diastereoselective Tandem Hetero-[5 + 2] Cycloaddition/
Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes. J.
Am. Chem. Soc. 2011, 133, 7304−7307. (c) Levin, S.; Nani, R. R.;
Reisman, S. E. Enantioselective Total Synthesis of (+)-Salvileucalin B.
J. Am. Chem. Soc. 2011, 133, 774−776. (d) Lian, Y.; Davies, H. M. L.
Combined C−H Functionalization/Cope Rearrangement with Vinyl
Ethers as a Surrogate for the Vinylogous Mukaiyama Aldol Reaction.
J. Am. Chem. Soc. 2011, 133, 11940−11943. (e) Davies, H. M. L.; Dai,
X.; Long, M. S. Combined C−H Activation/Cope Rearrangement as
a Strategic Reaction in Organic Synthesis: Total Synthesis of
(−)-Colombiasin A and (−)-Elisapterosin B. J. Am. Chem. Soc.
2006, 128, 2485−2490. (f) Lee, Y. R.; Hwang, J. C. Efficient
Synthesis of Five- and Seven-Membered-Ring Heterocycles by
Rhodium(II)-Catalyzed [3 + 2] and [3 + 4] Cycloaddition of
Diazocarbonyl Compounds with Conjugated Dienes. Eur. J. Org.
Chem. 2005, 2005, 1568−1577. (g) Nasveschuk, C. G.; Rovis, T.
Stereoselective Lewis acid mediated [1,3] ring contraction of 2,5-
dihydrooxepins as a route to polysubstituted cyclopentenes. Angew.
Chem., Int. Ed. 2005, 44, 3264−3267; Angew. Chem. 2005, 117,
3328−3331. (h) Hofmann, B.; Reissig, H.-U. Synthesis of function-
alized 2,5-dihydrooxepines by [3,3]-sigmatropic rearrangement of
cyclopropane derivatives. Synlett 1993, 1993, 27−29. (i) Hofmann,
B.; Reissig, H.-U. Swern Oxidation of Alkenyl-Substituted 2-(tert-
Butyldimethylsiloxy)-l-(hydroxymethy1)cyclopropanes: A Novel and
Flexibel Route to Functionalized 2,5-Dihydrooxepines. Chem. Ber.
1994, 127, 2327−2335. (j) Boeckman, R. K., Jr.; Shair, M. D.; Vargas,
J. R.; Stolz, L. A. Synthetic and Mechanistic Studies of the Retro-
Claisen Rearrangement. 2. A Facile Route to Medium-Ring
Heterocycles via Rearrangement of Vinylcyclopropane- and Cyclo-
butanecarboxaldehydes. J. Org. Chem. 1993, 58, 1295−1297.
(k) Boeckman, R. K., Jr.; Reeder, M. R. Synthetic and Mechanistic
Studies of the Retro-Claisen Rearrangement. 3. A Route to
Enantiomerically Pure Vinyl Cyclobutane Diesters via a Highly
Diastereoselective Syn SN2′ Reaction and Their Rearrangement to
Enantiomerically Pure Dihydrooxacenes. J. Org. Chem. 1997, 62,
6456−6457.
(10) (a) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. Expanding
the Scope of C−H Amination through Catalyst Design. J. Am. Chem.
Soc. 2004, 126, 15378−15379. (b) Gonzalez-Bobes, F.; Fenster, M. D.
B.; Kiau, S.; Kolla, L.; Kolotuchin, S.; Soumeillant, M. Rhodium-
catalyzed cyclopropanation of alkenes with dimethyl diazomalonate.
Adv. Synth. Catal. 2008, 350, 813−816.
(11) (a) Connell, R. D.; Tebbe, M.; Gangloff, A. R.; Helquist, P.;
Åkermark, B. Rhodium-catalyzed heterocycloaddition route to 1,3-
oxazoles as building blocks in natural products synthesis. Tetrahedron
1993, 49, 5445−5459. (b) Linder, J.; Garner, T. P.; Williams, H. E.
L.; Searle, M. S.; Moody, C. J. Telomestatin: Formal Total Synthesis
D
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