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Literature DB >> 29746119

Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams.

Abstract

In this Communication, we describe the construction of chiral α,β-unsaturated δ-lactams, widely used as pharmacophores, in high yields and excellent enantioselectivities using an oxidative relay Heck arylation reaction. This strategy also allows facile access to 7-substituted α,β-unsaturated ε-lactam products and δ-lactams containing a tetrasubstituted nitrogen-bearing stereocenter.

Entities: Chemical Disease Species

Mesh：

Substances：
Lactams
Palladium

Year: 2018 PMID： 29746119 PMCID： PMC5993423 DOI： 10.1021/jacs.8b02752

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

30 in total

1. Direct site-selective arylation of enamides via a decarboxylative cross-coupling reaction.

Authors: Nicolas Gigant; Laëtitia Chausset-Boissarie; Isabelle Gillaizeau
Journal: Org Lett Date: 2013-01-31 Impact factor: 6.005

2. Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives.

Authors: H Yanagisawa; S Ishihara; A Ando; T Kanazaki; S Miyamoto; H Koike; Y Iijima; K Oizumi; Y Matsushita; T Hata
Journal: J Med Chem Date: 1988-02 Impact factor: 7.446

3. Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products.

Authors: Carmen Escolano; Mercedes Amat; Joan Bosch
Journal: Chemistry Date: 2006-11-06 Impact factor: 5.236

4. Asymmetric vinylogous Mannich reactions: a versatile approach to functionalized heterocycles.

Authors: Shu-Tang Ruan; Jie-Min Luo; Yu Du; Pei-Qiang Huang
Journal: Org Lett Date: 2011-08-19 Impact factor: 6.005

5. Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors: Harshkumar H Patel; Matthew S Sigman
Journal: J Am Chem Soc Date: 2015-03-09 Impact factor: 15.419

6. Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization.

Authors: Ming Chen; Guangbin Dong
Journal: J Am Chem Soc Date: 2017-06-06 Impact factor: 15.419

7. Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors: Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal: J Am Chem Soc Date: 2016-12-01 Impact factor: 15.419

8. γ-Carbon Activation through N-Heterocyclic Carbene/Brønsted Acids Cooperative Catalysis: A Highly Enantioselective Route to δ-Lactams.

Authors: Yonglong Xiao; Jinxin Wang; Wenjing Xia; Shuangjie Shu; Shenchao Jiao; Yu Zhou; Hong Liu
Journal: Org Lett Date: 2015-07-27 Impact factor: 6.005

9. Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

Authors: Kentaro Takada; Taisuke Uehara; Yoichi Nakao; Shigeki Matsunaga; Rob W M van Soest; Nobuhiro Fusetani
Journal: J Am Chem Soc Date: 2004-01-14 Impact factor: 15.419

10. Asymmetric synthesis of delta-substituted alpha,beta-unsaturated delta-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines.

Authors: Claudio Fiorelli; Diego Savoia
Journal: J Org Chem Date: 2007-07-11 Impact factor: 4.354

9 in total

Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams.

1. Direct site-selective arylation of enamides via a decarboxylative cross-coupling reaction.

2. Angiotensin-converting enzyme inhibitors. 2. Perhydroazepin-2-one derivatives.

3. Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products.

4. Asymmetric vinylogous Mannich reactions: a versatile approach to functionalized heterocycles.

5. Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

6. Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization.

7. Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

8. γ-Carbon Activation through N-Heterocyclic Carbene/Brønsted Acids Cooperative Catalysis: A Highly Enantioselective Route to δ-Lactams.

9. Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

10. Asymmetric synthesis of delta-substituted alpha,beta-unsaturated delta-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines.

1. Rate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction.

2. 11-Step Total Synthesis of Teleocidins B-1-B-4.

3. Asymmetric δ-Lactam Synthesis with a Monomeric Streptavidin Artificial Metalloenzyme.

4. Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates.

5. Three-component vicinal-diarylation of alkenes via direct transmetalation of arylboronic acids.

6. Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.

7. 2-Fluoro-5-nitrophenyldiazonium: A Novel Sanger-Type Reagent for the Versatile Functionalization of Alcohols.

8. Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives.

Review 9. Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.