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Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins
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| Zeitschriftentitel: | Angewandte Chemie |
|---|---|
| Personen und Körperschaften: | , , , |
| In: | Angewandte Chemie, 132, 2020, 1, S. 259-264 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
|
| Schlagwörter: |
| author_facet |
Plamondon, Samuel J. Warnica, Josephine M. Kaldre, Dainis Gleason, James L. Plamondon, Samuel J. Warnica, Josephine M. Kaldre, Dainis Gleason, James L. |
|---|---|
| author |
Plamondon, Samuel J. Warnica, Josephine M. Kaldre, Dainis Gleason, James L. |
| spellingShingle |
Plamondon, Samuel J. Warnica, Josephine M. Kaldre, Dainis Gleason, James L. Angewandte Chemie Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins General Medicine |
| author_sort |
plamondon, samuel j. |
| spelling |
Plamondon, Samuel J. Warnica, Josephine M. Kaldre, Dainis Gleason, James L. 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.201911952 <jats:title>Abstract</jats:title><jats:p>Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (<jats:italic>E</jats:italic>)‐polyenes to form <jats:italic>trans</jats:italic>‐decalin ring systems are well precedented, highly enantioselective cyclizations of (<jats:italic>Z</jats:italic>)‐polyenes to form the corresponding <jats:italic>cis</jats:italic>‐decalins have not been reported. Here, we describe the first application of iminium catalysis to the initiation of polyene cyclizations. Ethyl 1,2‐diazepane‐1‐carboxylate catalyzes the cyclization of polyenes bearing enal initiators. Moreover, chiral bicyclic hydrazides catalyze the cyclizations of (<jats:italic>Z</jats:italic>)‐polyene substrates to form <jats:italic>cis</jats:italic>‐decalins with enantioselectivities of up to 97:3 er. DFT calculations suggest the catalysts promote the reaction by stabilizing positive charge as it develops during the bicyclization.</jats:p> Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of <i>cis</i>‐Decalins Angewandte Chemie |
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10.1002/ange.201911952 |
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| title |
Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_unstemmed |
Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_full |
Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_fullStr |
Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_full_unstemmed |
Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_short |
Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_sort |
hydrazide‐catalyzed polyene cyclization: asymmetric organocatalytic synthesis of <i>cis</i>‐decalins |
| topic |
General Medicine |
| url |
http://dx.doi.org/10.1002/ange.201911952 |
| publishDate |
2020 |
| physical |
259-264 |
| description |
<jats:title>Abstract</jats:title><jats:p>Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (<jats:italic>E</jats:italic>)‐polyenes to form <jats:italic>trans</jats:italic>‐decalin ring systems are well precedented, highly enantioselective cyclizations of (<jats:italic>Z</jats:italic>)‐polyenes to form the corresponding <jats:italic>cis</jats:italic>‐decalins have not been reported. Here, we describe the first application of iminium catalysis to the initiation of polyene cyclizations. Ethyl 1,2‐diazepane‐1‐carboxylate catalyzes the cyclization of polyenes bearing enal initiators. Moreover, chiral bicyclic hydrazides catalyze the cyclizations of (<jats:italic>Z</jats:italic>)‐polyene substrates to form <jats:italic>cis</jats:italic>‐decalins with enantioselectivities of up to 97:3 er. DFT calculations suggest the catalysts promote the reaction by stabilizing positive charge as it develops during the bicyclization.</jats:p> |
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| author | Plamondon, Samuel J., Warnica, Josephine M., Kaldre, Dainis, Gleason, James L. |
| author_facet | Plamondon, Samuel J., Warnica, Josephine M., Kaldre, Dainis, Gleason, James L., Plamondon, Samuel J., Warnica, Josephine M., Kaldre, Dainis, Gleason, James L. |
| author_sort | plamondon, samuel j. |
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| description | <jats:title>Abstract</jats:title><jats:p>Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (<jats:italic>E</jats:italic>)‐polyenes to form <jats:italic>trans</jats:italic>‐decalin ring systems are well precedented, highly enantioselective cyclizations of (<jats:italic>Z</jats:italic>)‐polyenes to form the corresponding <jats:italic>cis</jats:italic>‐decalins have not been reported. Here, we describe the first application of iminium catalysis to the initiation of polyene cyclizations. Ethyl 1,2‐diazepane‐1‐carboxylate catalyzes the cyclization of polyenes bearing enal initiators. Moreover, chiral bicyclic hydrazides catalyze the cyclizations of (<jats:italic>Z</jats:italic>)‐polyene substrates to form <jats:italic>cis</jats:italic>‐decalins with enantioselectivities of up to 97:3 er. DFT calculations suggest the catalysts promote the reaction by stabilizing positive charge as it develops during the bicyclization.</jats:p> |
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| imprint_str_mv | Wiley, 2020 |
| institution | DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-D161 |
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| spelling | Plamondon, Samuel J. Warnica, Josephine M. Kaldre, Dainis Gleason, James L. 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.201911952 <jats:title>Abstract</jats:title><jats:p>Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (<jats:italic>E</jats:italic>)‐polyenes to form <jats:italic>trans</jats:italic>‐decalin ring systems are well precedented, highly enantioselective cyclizations of (<jats:italic>Z</jats:italic>)‐polyenes to form the corresponding <jats:italic>cis</jats:italic>‐decalins have not been reported. Here, we describe the first application of iminium catalysis to the initiation of polyene cyclizations. Ethyl 1,2‐diazepane‐1‐carboxylate catalyzes the cyclization of polyenes bearing enal initiators. Moreover, chiral bicyclic hydrazides catalyze the cyclizations of (<jats:italic>Z</jats:italic>)‐polyene substrates to form <jats:italic>cis</jats:italic>‐decalins with enantioselectivities of up to 97:3 er. DFT calculations suggest the catalysts promote the reaction by stabilizing positive charge as it develops during the bicyclization.</jats:p> Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of <i>cis</i>‐Decalins Angewandte Chemie |
| spellingShingle | Plamondon, Samuel J., Warnica, Josephine M., Kaldre, Dainis, Gleason, James L., Angewandte Chemie, Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins, General Medicine |
| title | Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_full | Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_fullStr | Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_full_unstemmed | Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_short | Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| title_sort | hydrazide‐catalyzed polyene cyclization: asymmetric organocatalytic synthesis of <i>cis</i>‐decalins |
| title_unstemmed | Hydrazide‐Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis‐Decalins |
| topic | General Medicine |
| url | http://dx.doi.org/10.1002/ange.201911952 |