Allene chemistry
Editor: Prof. Kay M. Brummond
University of Pittsburgh
University of Pittsburgh
Even after decades of use, allenes can still be classified as an underutilized functional group. However, great advances in the chemistry of allenes have been made since the 1970s when they were regarded as difficult to prepare and very reactive, and not commonly encountered. Focusing on a particular functional group at first glance may seem trivial and obvious, but the importance of these types of studies is underscored by the fact that numerous Nobel prizes have been awarded for the study “alkenes in synthesis”. More importantly, transformations involving allenes can provide new scaffolds that lead to an expansion of chemical space where currently nearly half of all existing organic compounds can be described by a mere 143 molecular frameworks. This data supports the notion that we tend towards compounds and functionalities with which we are familiar and understand, but this, nevertheless, creates a limitation to our knowledge of our field.
CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands
- Shuxu Gao,
- Yu Liu and
- Shengming Ma
Beilstein J. Org. Chem. 2011, 7, 396–403, doi:10.3762/bjoc.7.51
Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.01,5]dodecenone
- Fuyuhiko Inagaki,
- Naoya Itoh,
- Yujiro Hayashi,
- Yumi Matsui and
- Chisato Mukai
Beilstein J. Org. Chem. 2011, 7, 404–409, doi:10.3762/bjoc.7.52
An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
- Ryuji Hayashi,
- John B. Feltenberger,
- Andrew G. Lohse,
- Mary C. Walton and
- Richard P. Hsung
Beilstein J. Org. Chem. 2011, 7, 410–420, doi:10.3762/bjoc.7.53
Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes
- Yu-Hsuan Wang,
- Joshua F. Bailey,
- Jeffrey L. Petersen and
- Kung K. Wang
Beilstein J. Org. Chem. 2011, 7, 496–502, doi:10.3762/bjoc.7.58
Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes
- Tomoya Miura,
- Tsuneaki Biyajima,
- Takeharu Toyoshima and
- Masahiro Murakami
Beilstein J. Org. Chem. 2011, 7, 578–581, doi:10.3762/bjoc.7.67
Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
- Yingdong Luo,
- Guozhu Zhang,
- Erik S. Hwang,
- Thomas A. Wilcoxon and
- Liming Zhang
Beilstein J. Org. Chem. 2011, 7, 596–600, doi:10.3762/bjoc.7.69
Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles
- Kay M. Brummond and
- Joshua M. Osbourn
Beilstein J. Org. Chem. 2011, 7, 601–605, doi:10.3762/bjoc.7.70
Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles
- Peter Wipf and
- Marija D. Manojlovic
Beilstein J. Org. Chem. 2011, 7, 824–830, doi:10.3762/bjoc.7.94
Toward an integrated route to the vernonia allenes and related sesquiterpenoids
- Da Xu,
- Michael A. Drahl and
- Lawrence J. Williams
Beilstein J. Org. Chem. 2011, 7, 937–943, doi:10.3762/bjoc.7.104
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