Categories: C-C Bond Formation > Cyclic compounds > Cyclic ketones
Synthesis of cyclobutanones
| Related: |
 |
 |
 |
Recent Literature
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.
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 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.
