A new halo aldol reaction: three-component reaction via 1,4-robust activation of ethynyl alkyl ketones for stereoselective formations of versatile aldol adducts.
[reaction: see text] A new three-component halo aldol reaction has been discovered for the tandem formations of I-C/C-C bonds by activating the alpha',beta-positions of alpha,beta-acetylenic ketones. The key intermediates, 1-iodo-3-siloxy-1,3-butadienes, were generated from allenolates and directly monitored by (1)H NMR spectroscopic analysis. Excellent geometric selectivity (>95%) and good yields (65-82%) have been achieved for 10 examples.
Wei
Han-Xun
HX
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Kim
Sun Hee
SH
Li
Guigen
G
D000447:Aldehydes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; C116609:3-hydroxybutanal