scholarly journals Iodine(III)-mediated halogenations of acyclic monoterpenoids

2018 ◽  
Vol 14 ◽  
pp. 1103-1111 ◽  
Author(s):  
Laure Peilleron ◽  
Tatyana D Grayfer ◽  
Joëlle Dubois ◽  
Robert H Dodd ◽  
Kevin Cariou
Keyword(s):  
Double Bond ◽  
Hypervalent Iodine ◽  
Halide Salt ◽  
Trisubstituted Double Bond ◽  
Excellent Selectivity

Five different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type chlorination of the distal trisubstituted double bond occurred with excellent selectivity and moderate to good yields.

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

The IX (X=O,N,C) Double Bond in Hypervalent Iodine Compounds: Is it Real?

2014 ◽  
Vol 53 (36) ◽  
pp. 9617-9621 ◽  
Author(s):  
Alexander S. Ivanov ◽  
Ivan A. Popov ◽  
Alexander I. Boldyrev ◽  
Viktor V. Zhdankin
Keyword(s):  
Double Bond ◽  
Hypervalent Iodine ◽  
Iodine Compounds

Total Synthesis of Amphidinolide X and Its 12Z-Isomer by Formation of the C12-C13 Trisubstituted Double Bond via Ring-Closing Metathesis

Synlett ◽  
2008 ◽  
Vol 2008 (11) ◽  
pp. 1737-1741 ◽  
Author(s):  
Wei-Min Dai ◽  
Jinlong Wu ◽  
Yile Chen ◽  
Jian Jin ◽  
Jianshu Lou ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Ring Closing Metathesis ◽  
Trisubstituted Double Bond

Selective Formation of a Z-Trisubstituted Double Bond Using a 1-(tert-Butyl)tetrazolyl Sulfone

2014 ◽  
Vol 79 (21) ◽  
pp. 10648-10654 ◽  
Author(s):  
Adriana Lorente ◽  
Fernando Albericio ◽  
Mercedes Álvarez
Keyword(s):  
Double Bond ◽  
Trisubstituted Double Bond ◽  
Tert Butyl ◽  
Selective Formation

Copper-catalyzed, hypervalent iodine mediated CC bond activation of enaminones for the synthesis of α-keto amides

2016 ◽  
Vol 52 (6) ◽  
pp. 1270-1273 ◽  
Author(s):  
Jie-Ping Wan ◽  
Yunfang Lin ◽  
Xiaoji Cao ◽  
Yunyun Liu ◽  
Li Wei
Keyword(s):  
Double Bond ◽  
Bond Activation ◽  
Hypervalent Iodine ◽  
General Synthesis

An unprecedented approach toward the general synthesis of α-keto amides has been established by tailoring the CC double bond of enaminones in the presence of CuI and hypervalent iodine.

ChemInform Abstract: CONJUGATE ACYLATION OF ALKYNES, A METHOD FOR THE SYNTHESIS OF α,β-UNSATURATED KETONES WITH A TRISUBSTITUTED DOUBLE BOND

1977 ◽  
Vol 8 (35) ◽  
pp. no-no
Author(s):  
A. A. SCHEGOLEV ◽  
W. A. SMIT ◽  
S. A. KHURSHUDYAN ◽  
V. A. CHERTKOV ◽  
V. F. KUCHEROV
Keyword(s):  
Double Bond ◽  
Unsaturated Ketones ◽  
Trisubstituted Double Bond
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