Irregularities in the Effect of Potassium Phosphate in Ynamide Synthesis

被引:68
作者
Dooleweerdt, Karin [1 ,2 ,3 ]
Birkedal, Henrik [1 ,2 ]
Ruhland, Thomas [3 ]
Skrydstrup, Troels [1 ,2 ]
机构
[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark
[2] Aarhus Univ, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus C, Denmark
[3] H Lundbeck & Co AS, Dept Med Chem & Support, DK-2400 Copenhagen, Denmark
基金
新加坡国家研究基金会;
关键词
D O I
10.1021/jo801935b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The yields of ynamides using Hsung's second generation protocol depend substantially on the quality of K3PO4. of K3PO4 from different suppliers were investigated by various techniques, revealing that the use Of pure and anhydrous K3PO4 provides higher ynamide yields in comparison to samples contaminated with hydrates (K3PO4 center dot 1.5H(2)O and K3PO4 center dot 7H(2)O). With high quality K3PO4, a number of ynamides were synthesized in yields of 52-91%. In addition. we report that ynamides can undergo regioselective hydroamination with carbamates.
引用
收藏
页码:9447 / 9450
页数:4
相关论文
共 36 条
[1]   Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation [J].
Al-Rashid, Ziyad F. ;
Hsung, Richard P. .
ORGANIC LETTERS, 2008, 10 (04) :661-663
[2]   Regiocontrolled carbometallation reactions of ynamides [J].
Chechik-Lankin, H ;
Livshin, S ;
Marek, I .
SYNLETT, 2005, (13) :2098-2100
[3]   Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].
Couty, S ;
Liégault, B ;
Meyer, C ;
Cossy, J .
ORGANIC LETTERS, 2004, 6 (15) :2511-2514
[4]   Chemoselective epoxidation of ene-ynamides:: Intramolecular cyclopropanation induced by the intermediate α-oxocarbene [J].
Couty, Sylvain ;
Meyer, Christophe ;
Cossy, Janine .
SYNLETT, 2007, (18) :2819-2822
[5]   Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides [J].
Couty, Sylvain ;
Meyer, Christophe ;
Cossy, Janine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6726-6730
[6]   Synthesis of highly substituted indolines and indoles via intramolecular [4+2] cycloaddition of ynamides and conjugated enynes [J].
Dunetz, JR ;
Danheiser, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5776-5777
[7]   Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols [J].
Frederick, MO ;
Hsung, RP ;
Lambeth, RH ;
Mulder, JA ;
Tracey, MR .
ORGANIC LETTERS, 2003, 5 (15) :2663-2666
[8]  
Glaser C., 1869, Chem. Ber, V2, P422, DOI DOI 10.1002/CBER.186900201183
[9]   Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives [J].
Hashmi, A. Stephen K. ;
Rudolph, Matthias ;
Bats, Jan W. ;
Frey, Wolfgang ;
Rominger, Frank ;
Oeser, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (22) :6672-6678
[10]   Synthesis of functionalized oxazolones by a sequence of Cu(II)- and Au(I)-catalyzed transformations [J].
Istrate, Florin M. ;
Buzas, Andrea K. ;
Jurberg, Igor Dias ;
Odabachian, Yann ;
Gagosz, Fabien .
ORGANIC LETTERS, 2008, 10 (05) :925-928