Enantio‐ and Diastereoselective Syntheses of 3‐Hydroxypiperidines through Iridium‐Catalyzed Allylic Substitution

Hoecker, Johannes; Rudolf, Georg C.; Bächle, Florian; Fleischer, Steffen; Lindner, Benjamin; Helmchen, Günter

doi:10.1002/ejoc.201300445

Cited by 18 publications

(5 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chiral 3-hydroxypiperidines 420 could be obtained in a highly stereoselective manner on the basis of epoxidation/ elimination reactions of piperidine derivatives obtained from diacylamines (Scheme 206). 307 The chiral N-methoxylactams, prepared as described above, could react with Grignard or organolithium reagents. 308 The obtained hemiaminals could be reduced diastereoselectively to give cis-2,5-piperidines (Scheme 207).…”

Section: Sulfonamidesmentioning

confidence: 99%

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

et al. 2018

Self Cite

View full text Add to dashboard Cite

In this review, we summarize the origin and advancements of iridiumcatalyzed asymmetric allylic substitution reactions during the past two decades. Since the first report in 1997, Ir-catalyzed asymmetric allylic substitution reactions have attracted intense attention due to their exceptionally high regio-and enantioselectivities. Ircatalyzed asymmetric allylic substitution reactions have been significantly developed in recent years in many respects, including ligand development, mechanistic understanding, substrate scope, and application in the synthesis of complex functional molecules. In this review, an explicit outline of ligands, mechanism, scope of nucleophiles, and applications is presented.

show abstract

Section: Sulfonamidesmentioning

confidence: 99%

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…Many acylated and sulfonylated nitrogen pronucleophiles also aminate aryl-substituted allylic carbonates, in which Hartwig and Pouy recently reviewed the use of phosphoramidite ligands in this capacity. 80 Other pronucleophiles utilized successfully in the enantioselective iridium-catalyzed allylic amination reaction include 2-bromobenzylamine, 81 indolines, 82 propargylic amines, 83,84 acrylamides 70,85 and cyclic aliphatic amines. 86…”

Section: Review Syn Thesis Scheme 14 Two Approaches To (S)-nicotine (mentioning

confidence: 99%

Recent Developments in Asymmetric Allylic Amination Reactions

2016

View full text Add to dashboard Cite

The asymmetric synthesis of allylic amines is an important research area in modern synthetic organic chemistry, primarily due to the inherent utility and ubiquity of this functional group in various synthetic intermediates and bioactive agents. For instance, a plethora of methods for the stereocontrolled construction of allylic amines now provides a vibrant array of strategies for the installation of this important functionality. This review highlights developments in the field since 1998 through the provision of the most important methods and their mechanistic aspects in order to provide insight into their current scope and limitations. Hence, we envisage it will be an essential guide to the current state-of-the-art for this important area, which highlights potential new opportunities for further developments.

show abstract

“…In 2013, Helmchen 73 reported a novel synthesis of Derythro-sphingosine (1) in nine linear steps and 5% overall yield (Scheme 42). The highlight of the scheme was a chiraliridium-catalyzed allylic amination to give the chiral carbamate 207 in high yield (87%) and excellent enantioselectivity (98%).…”

Section: Syn Thesismentioning

confidence: 99%

Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines

Gao

Ding

et al. 2016

Synthesis

View full text Add to dashboard Cite

Sphingolipids and their derivatives such as glycosphingolipids and sphingomyelins exist ubiquitously in biomembrane of all eukaryotic cells, which play pivotal roles in cell proliferation, recognition, adhesion, and signal transduction. Sphingosine is shown to be the important lipid moiety in the large majority of glycosphingolipids and sphingomyelins, while phytosphingosine is one of the major long-chain moieties of glycosphingolipids. Due to the significance of the two bioactive lipids, tremendous efforts have been made to synthesize sphingosine or phytosphingosine using chiral pool approaches, chiral auxiliary and asymmetric reactions to construct the continuous stereogenic centers in them. This review covers the synthetic literatures published in the year after 2000.

show abstract

Enantio‐ and Diastereoselective Syntheses of 3‐Hydroxypiperidines through Iridium‐Catalyzed Allylic Substitution

Cited by 18 publications

References 59 publications

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

Recent Developments in Asymmetric Allylic Amination Reactions

Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines

Contact Info

Product

Resources

About