Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones.
Basdevant B1, Legault CY1.
The Journal of organic chemistry.J Org Chem.2015 Jul 2;80(13):6897-902. doi: 10.1021/acs.joc.5b00948. Epub 2015 Jun 22.
The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of th
Syntheses of Dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1 via Diastereoselective Epoxidation of N-Protected 4-Aminocyclohex-2-en-1-ols.
Brennan MB1, Csatayová K1, Davies SG1, Fletcher AM1, Green WD1, Lee JA1, Roberts PM1, Russell AJ1, Thomson JE1.
The Journal of organic chemistry.J Org Chem.2015 Jul 2;80(13):6609-18. doi: 10.1021/acs.joc.5b00716. Epub 2015 Jun 15.
Diastereoselective syntheses of dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1 have been achieved from N-protected 4-aminocyclohex-2-en-1-ols via two complementary procedures for epoxidation as the key step. Treatment of either trans- or cis-4-N-benzylaminocyclohex-2-en-1-ol with Cl3CCO2H and
Iodoarene-Catalyzed Stereospecific Intramolecular sp(3) C-H Amination: Reaction Development and Mechanistic Insights.
Zhu C1, Liang Y, Hong X, Sun H1, Sun WY1, Houk KN, Shi Z1.
Journal of the American Chemical Society.J Am Chem Soc.2015 Jun 24;137(24):7564-7. doi: 10.1021/jacs.5b03488. Epub 2015 Jun 11.
A new strategy is reported for intramolecular sp(3) C-H amination under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calcu
Oxidative cleavage of carbon–carbon double bonds to carbonyl compounds is an essential operation in organic synthesis. Ozonolysis is generally accepted as the standard method for this direct tra …