Categories: C-C Bond Formation > Carbocyclic compounds > Cyclic ketones
Synthesis of cyclobutanones
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Recent Literature
A catalytic protio-semipinacol ring-expansion reaction for the highly
enantioselective conversion of tertiary vinylic cyclopropyl alcohols into
cyclobutanone products bearing α-quaternary stereogenic centers relies on the
cocatalytic effect of a chiral dual-hydrogen-bond donor (HBD) with hydrogen
chloride. In a stepwise mechanism, protonation of the alkene is followed by C-C
bond migration.
M. A. S. Blackburn, C. C. Wagen, M. R. Bodrogean, P. M. Tadross, A. J.
Bendelsmith, D. A. Kutateladze, E. N. Jacobsen, J. Am. Chem. Soc.,
2023, 145, 15036-15042.
Hydroboration of 1-alkynyl-1-boronate esters and in situ transmetalation furnishes
1-alkenyl-1,1-borozinc heterobimetallic intermediates. Reaction with aldehydes
and in situ cyclopropanation generates B(pin) substituted cyclopropyl carbinols
with excellent diastereoselectivities. Oxidation provides trisubstituted
α-hydroxycyclopropyl carbinols, that allow access to both cis- and
trans-2,3-disubstituted cyclobutanones via a facile pinacol-type
rearrangement.
M. M. Hussain, H. Li, N. Hussain, M. Ureņa, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2009,
131, 6516-6524.
M. M. Hussain, H. Li, N. Hussain, M. Ureņa, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2009,
131, 6516-6524.
Chiral complexes developed previously for asymmetric additions of nucleophiles
to π-allylpalladium complexes are excellent in controlling enantioselectivity in
Wagner-Meerwein shifts. The versatility of the access to the requisite
substrates and the functionality of the obtained products should make this
approach an attractive asymmetric synthetic strategy.
B. M. Trost, T. Yasukata, J. Am. Chem. Soc., 2001,
123, 7162-7163.
Chemoselective C-C bond cleavages of reactive bicyclo[1.1.1]pent-1-yl alcohols (BCP-OHs)
provide cyclobutanone derivatives through a base-mediated single C-C bond
cleavage or α,β-unsaturated ketones by palladium-catalyzed dual C-C bond
cleavage.
Y. Ma, Y. Ai, S. Yu, Synlett, 2023,
34,
149-152.
Oxidative ring expansion of methylenecyclopropanes with CAN under oxygen
atmosphere was investigated. A facile conversion affording
2,2-diarylcyclobutanones occurred in good yields.
V. Nair, T. D. Suja, K. Mohanan, Synthesis, 2006, 2531-2534.
A catalytic radical process enables an asymmetric 1,4-C-H alkylation of
diazoketones for stereoselective construction of cyclobutanone structures. The
key to success is the optimization of the Co(II)-based metalloradical catalyst
through judicious modulation of a D2-symmetric chiral amidoporphyrin ligand to
adopt proper steric, electronic, and chiral environments.
J. Xie, P. Xu, Y. Zhu, J. Wang, W.-C. C. Lee, X. P. Zhang, J. Am. Chem. Soc.,
2021, 143, 11337-11344.
A stereospecific gold(I)-catalyzed rearrangement of 1-alkynyl cyclobutanols and
cyclopropanols provides alkylidene cycloalkanones. The reaction tolerates
terminal alkynes as well as alkyl, aryl, and halo-substitution at the acetylenic
position and substituents on the ring.
J. P. Markham, S. T. Staben, F. D. Toste, J. Am. Chem. Soc., 2005,
127, 9708-9709.
Visible-Light-Induced Aza-Pinacol Rearrangement: Ring Expansion of
Alkylidenecyclopropanes
W.-D. Liu, G.-Q. Xu, X.-Q. Hu, P.-F. Xu, Org. Lett.,
2017, 19, 6288-6291.
Halocycloalkenones are potent dienophiles in Diels-Alder cycloadditions.
2-Brominated cycloalkenone dienophiles are highly endo selective and
significantly more reactive than their nonhalogenated parent compounds. A
base-mediated reaction enables the facile conversion of brominated cyclobutanone
Diels-Alder adducts to synthetically useful cyclopropyl derivatives.
A. G. Ross, S. D. Townsend, S. J. Danishefsky, J. Org. Chem., 2013,
78, 204-210.