Asymmetric synthesis of allylic compounds via hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes

Chemical Society Reviews
Guanlin LiWanbin Zhang

Abstract

Hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes are widely utilized in the synthesis of valuable allylic compounds. In the past decades, asymmetric catalysis has emerged as one of the most attractive fields in organic synthesis. Recently, the asymmetric versions of hydrofunctionalisation and difunctionalisation reactions have become powerful and compelling tools to afford enantiopure allylic compounds, appealing to a large range of chemists. Various metal complexes modified with a large number of chiral ligands and several chiral organocatalysts have been developed to promote the hydrofunctionalisation and difunctionalisation reactions and expand substrate scope. This review provides an overview of this field, and aims at summarizing the chiral ligand used in this area of research. A detailed discussion of the development of these reactions and the general reaction mechanisms is provided.

References

Jun 1, 1990·Environmental Health Perspectives·N L Morrow
Jul 13, 2000·Accounts of Chemical Research·G Helmchen, A Pfaltz
Jul 18, 2001·Accounts of Chemical Research·X LuZ Xu
Jul 18, 2001·Journal of the American Chemical Society·O LöberJ F Hartwig
Dec 26, 2001·Chemical Reviews·R ZimmerF A Khan
Dec 26, 2001·Chemical Reviews·T Kondo, T A Mitsudo Ta
Feb 1, 1996·Chemical Reviews·Barry M. Trost, David L. Van Vranken
Feb 19, 2002·Chemical Reviews·Thomas E. Müller, Matthias Beller
Apr 4, 2002·Journal of the American Chemical Society·Jan PawlasJohn F Hartwig
Jul 4, 2002·Journal of the American Chemical Society·Sukwon Hong, Tobin J Marks
Apr 10, 2003·Chemical Society Reviews·Frauke Pohlki, Sven Doye
Apr 10, 2003·Chemical Reviews·Jan C Namyslo, Dieter E Kaufmann
Apr 10, 2003·Journal of the American Chemical Society·Barry M TrostBernd Plietker
Aug 14, 2003·Chemical Reviews·T V RajanBabu
Sep 25, 2003·Journal of the American Chemical Society·Lutz AckermannRebecca N Loy
Feb 12, 2004·Journal of the American Chemical Society·Léopold M LuteteYoshinori Yamamoto
Jun 10, 2004·Chemical Reviews·Francisco AlonsoMiguel Yus
Sep 25, 2004·Bioorganic & Medicinal Chemistry·Kazuhiko TorisuMasaaki Toda
Oct 23, 2004·The Journal of Organic Chemistry·Andreas LeitnerJohn F Hartwig
Dec 17, 2004·Journal of the American Chemical Society·Nicholas F PelzJames P Morken
Oct 1, 2005·Chemistry : a European Journal·Barry M TrostJia Xie
Jan 5, 2006·Journal of the American Chemical Society·Joshua D Sieber, James P Morken
Feb 24, 2006·Journal of the American Chemical Society·Takahiro NishimuraTamio Hayashi
May 4, 2006·Journal of the American Chemical Society·Barry M Trost, Jia Xie
May 20, 2006·The Journal of Organic Chemistry·Nitin T PatilYoshinori Yamamoto
Jun 26, 2007·Journal of the American Chemical Society·Heather E BurksJames P Morken
Jul 20, 2007·The Journal of Organic Chemistry·Nitin T PatilYoshinori Yamamoto
Sep 7, 2007·Journal of the American Chemical Society·Haifeng DuYian Shi
Oct 9, 2007·Journal of the American Chemical Society·Wei Zeng, Sherry R Chemler
Oct 16, 2007·Chemistry, an Asian Journal·Justin T Mohr, Brian M Stoltz
Oct 31, 2007·Angewandte Chemie·Zhan Lu, Shengming Ma

❮ Previous
Next ❯

Citations

Sep 18, 2020·Organic & Biomolecular Chemistry·Jun-Fa HanKe-Yin Ye
Aug 7, 2020·Chemical Society Reviews·Huan-Ming HuangFrank Glorius
Oct 10, 2020·Chemical Science·Ping YangShu-Li You
Jan 8, 2021·Angewandte Chemie·Ryan T DavisonVy M Dong
Jan 14, 2021·Organic Letters·Min-Song WuLiu-Zhu Gong
Jan 23, 2021·Organic Letters·Rongrong YuXianjie Fang
Feb 25, 2021·Organic & Biomolecular Chemistry·Linqing WangDongxu Yang
Mar 12, 2021·Journal of the American Chemical Society·Fu-Dong LuWen-Jing Xiao
Mar 19, 2021·Journal of the American Chemical Society·Ben-Xian XiaoYing-Chun Chen
Mar 17, 2021·Journal of the American Chemical Society·Xiaobo PangXing-Zhong Shu
Mar 30, 2021·European Journal of Organic Chemistry·Katharina RodeAlexander Breder
May 11, 2021·Journal of the American Chemical Society·Shao-Qian YangZhi-Tao He
Jul 14, 2021·Journal of the American Chemical Society·Christopher J C CoozeRylan J Lundgren
Aug 12, 2021·Journal of the American Chemical Society·Jun ChenJia-Rong Chen
Aug 18, 2021·Journal of the American Chemical Society·Yin-Lin LiJunliang Zhang
Aug 11, 2021·Chemistry : a European Journal·Pan-Pan GaoJia-Rong Chen
Sep 23, 2021·ACS Omega·Leandros P ZorbaGeorgios C Vougioukalakis
Sep 11, 2021·Chemistry : a European Journal·Chengdong WangKuiling Ding

❮ Previous
Next ❯

Methods Mentioned

BETA
hydroamination
hydroaminations
X-ray
diamination
hydroacylation

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.