Categories: C-C Bond Formation > Carbocyclic compounds > Cyclic enones
Synthesis of cyclobutenones
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Recent Literature
A tandem Michael addition/cyclic 1,2-addition/elimination of 2,3-allenoates and
organozinc reagents enables the synthesis of polysubstituted cyclobutenones,
which are not readily available from traditional methods due to the intrinsic
ring strain. Application to the synthesis of stereodefined β,γ-unsaturated
enones is demonstrated.
G. Chai, S. Wu, C. Fu, S. Ma, J. Am. Chem. Soc., 2011,
133, 3740-3743.
A one-pot synthesis of 4-amino-2-naphthol derivatives is accomplished via a ZnI2-catalyzed
tandem Friedel-Crafts reaction sequence. While in the presence of Pd(0) catalyst,
a [2 + 2] cycloaddition reaction of ynamides with monosubstituted ketenes
provides 3-aminocyclobutenones, which were subsequently converted to
3-amino-1-naphthols.
C. Qian, K. Liu, S.-W. Tao, F.-L. Zhang, Y.-M. Zhu, S.-L. Yang, J. Org. Chem., 2018, 83,
9201-9209.