The DOI matches its Crossref record; 32 of the 32 references it cites were found in a registry or an index.
Reversal of Regioselectivity in Ynamide Chemistry
Abstract
Ynamides are special alkynes bearing an electron-withdrawing group on the nitrogen atom, and they have been extensively studied over the past decade. However, the addition of functional groups across ynamides in these transformations typically occurs at the α-position of the ynamide because of the strong polarization of the alkynyl moiety. Studies of umpolung transformations in ynamide chemistry may not only discover organic reactions but also lead to divergent organic syntheses, thus significantly enriching ynamide chemistry. This review summarizes four main strategies utilized to achieve reversal of the regioselectivity, including the ring strain factor, metal–carbonyl (or sulfonyl) chelation, and base-mediated and radical-initiated addition.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Ynamides: A Modern Functional Group for the New Millennium
DeKorver, K. A., Li, H., Lohse, A. G., Hayashi, R., Lu, Z., Zhang, Y., & Hsung, R. P. (2010) · Chemical Reviews · doi:10.1021/cr100003s · Cited by 886
Ynamides: Versatile Tools in Organic Synthesis
Evano, G., Coste, A., & Jouvin, K. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200905817 · Cited by 812
Ynamides in Ring Forming Transformations
Wang, X.-N., Yeom, H.-S., Fang, L.-C., He, S., Ma, Z.-X., Kedrowski, B. L., & Hsung, R. P. (2014) · Accounts of Chemical Research · doi:10.1021/ar400193g · Cited by 605
Pan, F., Shu, C., & Ye, L.-W. (2016) · Organic & Biomolecular Chemistry · doi:10.1039/c6ob01774f · Cited by 270
Self-citationYnamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis
Hu, L., Xu, S., Zhao, Z., Yang, Y., Peng, Z., Yang, M., Wang, C., & Zhao, J. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b07230 · Cited by 267
Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge–accelerated sulfonium rearrangement
Kaldre, D., Klose, I., & Maulide, N. (2018) · Science · doi:10.1126/science.aat5883 · Cited by 233
A unique approach to aldol products for the creation of all-carbon quaternary stereocentres
Das, J. P., Chechik, H., & Marek, I. (2009) · Nature Chemistry · doi:10.1038/nchem.131 · Cited by 186
Li, J., & Neuville, L. (2013) · Organic Letters · doi:10.1021/ol400560m · Cited by 160
Gourdet, B., & Lam, H. W. (2009) · Journal of the American Chemical Society · doi:10.1021/ja900946h · Cited by 152
Synthesis of Functionalized Oxazolones by a Sequence of Cu(II)- and Au(I)-Catalyzed Transformations
Istrate, F. M., Buzas, A. K., Jurberg, I. D., Odabachian, Y., & Gagosz, F. (2008) · Organic Letters · doi:10.1021/ol703077g · Cited by 143
Fukudome, Y., Naito, H., Hata, T., & Urabe, H. (2008) · Journal of the American Chemical Society · doi:10.1021/ja078163b · Cited by 139
Gold-Catalyzed Cyclization of N-Alkynyl Carbamates
Hashmi, A. S. K., Salathé, R., & Frey, W. U. (2007) · Synlett · doi:10.1055/s-2007-982562 · Cited by 126
Computational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization
Straker, R. N., Peng, Q., Mekareeya, A., Paton, R. S., & Anderson, E. A. (2016) · Nature Communications · doi:10.1038/ncomms10109 · Cited by 121
The First Stereoselective Ficini−Claisen Rearrangement Using Chiral Ynamides
Mulder, J. A., Hsung, R. P., Frederick, M. O., Tracey, M. R., & Zificsak, C. A. (2002) · Organic Letters · doi:10.1021/ol020037j · Cited by 117
Li, L., Chen, X., Wang, Z., Zhou, B., Liu, X., Lü, X., & Ye, L. (2017) · ACS Catalysis · doi:10.1021/acscatal.7b01038 · Cited by 117
Self-citationYnamide‐Mediated Thiopeptide Synthesis
Yang, J., Wang, C., Xu, S., & Zhao, J. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201811586 · Cited by 101
Regiocontrolled Palladium-Catalyzed Arylative Cyclizations of Alkynols
Fujino, D., Yorimitsu, H., & Osuka, A. (2014) · Journal of the American Chemical Society · doi:10.1021/ja5029028 · Cited by 98
Gourdet, B., Rudkin, M. E., Watts, C., & Lam, H. W. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo901658v · Cited by 91
One‐Pot Multicomponent Synthesis of β‐Amino Amides
Huang, B., Zeng, L., Shen, Y., & Cui, S. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201700840 · Cited by 84
Catalytic Ynamide Oxidation Strategy for the Preparation of α-Functionalized Amides
Pan, F., Li, X., Chen, X., Shu, C., Ruan, P., Shen, C., Lü, X., & Ye, L. (2016) · ACS Catalysis · doi:10.1021/acscatal.6b01599 · Cited by 75
Self-citationFadel, A., Legrand, F., Evano, G., & Rabasso, N. (2011) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201000792 · Cited by 61
Rhodium-catalyzed carbometalation of ynamides with organoboron reagents
Gourdet, B., Smith, D. L., & Lam, H. W. (2010) · Tetrahedron · doi:10.1016/j.tet.2010.06.021 · Cited by 60
Transition‐Metal‐Free Tunable Chemoselective N Functionalization of Indoles with Ynamides
Hentz, A., Retailleau, P., Gandon, V., Cariou, K., & Dodd, R. H. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201402767 · Cited by 59
Ynamide Preactivation Allows a Regio‐ and Stereoselective Synthesis of α,β‐Disubstituted Enamides
Baldassari, L. L., de la Torre, A., Li, J., Lüdtke, D. S., & Maulide, N. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201709128 · Cited by 59
Intramolecular Carbocupration of N-Aryl-ynamides: A Modular Indole Synthesis
Gati, W., Couty, F., Boubaker, T., Rammah, M. M., Rammah, M. B., & Evano, G. (2013) · Organic Letters · doi:10.1021/ol4013298 · Cited by 57
Gourdet, B., & Lam, H. W. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201004328 · Cited by 57
Rhodium-Catalyzed Annulation of Ynamides with Bifunctional Arylboron Reagents
Gourdet, B., Rudkin, M. E., & Lam, H. W. (2010) · Organic Letters · doi:10.1021/ol100769p · Cited by 53
Liu, H., Yang, Y., Wu, J., et al. (2016) · Chemical Communications · doi:10.1039/c6cc01565d · Cited by 53
Yasui, H., Yorimitsu, H., & Oshima, K. (2008) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.81.373 · Cited by 48
Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids
Moskowitz, M., & Wolf, C. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201814074 · Cited by 43
Peng, Z., Zhang, Z., Tu, Y., Zeng, X., & Zhao, J. (2018) · Organic Letters · doi:10.1021/acs.orglett.8b02409 · Cited by 26
Anitha, M., Shankar, M., & Swamy, K. C. K. (2019) · Organic Chemistry Frontiers · doi:10.1039/c9qo00027e · Cited by 16
Cited by
Ynamide-Mediated Thionoester and Dithioester Syntheses
Yao, C., Yang, J., Lu, X., Zhang, S., & Zhao, J. (2020) · Organic Letters · doi:10.1021/acs.orglett.0c02402 · Cited by 35
Metadata
- Authors
- Zhou, B., Tan, T.-D., Zhu, X.-Q., Shang, M., & Ye, L.-W.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-06-05
- Volume
- 9
- Issue
- 7
- Pages
- 6393-6406
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2948495562
- Cited by
- 294
- References
- 32
- FWCI
- 15.12
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
