Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.

Organic Letters
Chao JiangM Christina White

Abstract

Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under Pd(II)/sulfoxide-catalysis that furnishes a wide range of α- and β-homophenylalanine precursors from commodity α-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated.

References

Nov 20, 1980·Nature·A A PatchettC A Stone
Jan 9, 1984·FEBS Letters·M R AttwoodW A Thomas
May 31, 1996·The Journal of Organic Chemistry·Richard C. LarockKarl P. Peterson
Mar 16, 2002·The Journal of Organic Chemistry·Philip N CollierRichard J K Taylor
Jan 14, 2005·Organic Letters·Kenneth J FraunhofferM Christina White
May 12, 2005·Journal of the American Chemical Society·Mark S ChenM Christina White
Jan 13, 2006·The New England Journal of Medicine·Fan Fan HouRen Wen Geng
Jan 20, 2006·Hypertension Research : Official Journal of the Japanese Society of Hypertension·Eiichi GeshiTakashi Katagiri
Feb 25, 2006·The Journal of Organic Chemistry·Bradley A SteinhoffShannon S Stahl
Jul 13, 2006·Journal of the American Chemical Society·Kenneth J FraunhofferM Christina White
Nov 23, 2006·Journal of the American Chemical Society·Jared H Delcamp, M Christina White
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
Jan 30, 2007·Accounts of Chemical Research·Gary A Molander, Noel Ellis
May 23, 2007·Journal of the American Chemical Society·Kenneth J Fraunhoffer, M Christina White
Oct 9, 2007·Journal of the American Chemical Society·Hélène LebelLise Bréthous
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Feb 28, 2008·Journal of the American Chemical Society·Sean A Reed, M Christina White
Jun 3, 2008·Chemistry : a European Journal·Kim Huard, Hélène Lebel
Jul 12, 2008·Accounts of Chemical Research·Jared C LewisJonathan A Ellman
Jul 16, 2008·Angewandte Chemie·Dustin J Covell, M Christina White
Aug 2, 2008·Journal of the American Chemical Society·Jared H DelcampM Christina White
Sep 10, 2008·Journal of the American Chemical Society·Song LinZhang-Jie Shi
Oct 4, 2008·Journal of the American Chemical Society·Andrew J Young, M Christina White
Mar 21, 2009·Science·Robert J Phipps, Matthew J Gaunt
Aug 4, 2009·Journal of the American Chemical Society·Grant T Rice, M Christina White
Aug 4, 2009·Journal of the American Chemical Society·Sean A ReedM Christina White
Oct 2, 2009·Chemistry : a European Journal·Fady NahraGiovanni Poli
Nov 27, 2009·Chemical Reviews·Graham E Dobereiner, Robert H Crabtree
Jan 22, 2010·The New England Journal of Medicine·John J V McMurray
Jan 27, 2010·Organic Letters·William H HendersonJames P Stambuli
Jan 30, 2010·Science·Mark S Chen, M Christina White
Feb 10, 2010·The Journal of Organic Chemistry·Emilie ThieryJacques Muzart
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
Jul 29, 2010·Journal of the American Chemical Society·Nicolaas A VermeulenM Christina White
Sep 23, 2010·Journal of the American Chemical Society·Erik W Werner, Matthew S Sigman
Feb 24, 2011·Angewandte Chemie·Erik M Stang, M Christina White

❮ Previous
Next ❯

Citations

Jul 12, 2014·Tetrahedron·Dustin J Covell, M Christina White
Dec 18, 2015·Organic Letters·Heng ZhangShang-Dong Yang
May 4, 2016·Journal of the American Chemical Society·Peng HuDavid Milstein
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Dec 3, 2016·Angewandte Chemie·Andreas Uwe MeyerBurkhard König
Feb 16, 2017·Chemical Communications : Chem Comm·Ana SirventMiguel Yus
May 9, 2015·Chemical Society Reviews·Gellért SiposReto Dorta
Dec 7, 2017·Chemical Communications : Chem Comm·Chunsheng LiHuanfeng Jiang
Mar 7, 2019·Organic & Biomolecular Chemistry·Yunlong Guo, Zengming Shen
Apr 12, 2019·Organic & Biomolecular Chemistry·Da Seul Lee, Eun Jin Cho
May 24, 2014·Organic & Biomolecular Chemistry·Xu Zhu, Shunsuke Chiba
Jul 14, 2016·Angewandte Chemie·Alexander P Pulis, David J Procter
May 6, 2017·Organic & Biomolecular Chemistry·Dongdong LiangFengtian Xue
Jul 24, 2013·Chemistry : a European Journal·Timothy W Liwosz, Sherry R Chemler
Apr 16, 2014·Organic & Biomolecular Chemistry·Huoji ChenHuanfeng Jiang
May 29, 2014·Chemical Communications : Chem Comm·Huanfeng JiangWanqing Wu
Sep 8, 2017·The Journal of Organic Chemistry·Chunsheng LiHuanfeng Jiang
Feb 14, 2015·The Journal of Organic Chemistry·Huayou HuChao Wang
Jun 26, 2014·The Journal of Organic Chemistry·Kohei WatanabeMasami Sakamoto
Feb 20, 2013·Journal of the American Chemical Society·Tiezheng JiaPatrick J Walsh
Dec 21, 2012·Organic Letters·Hui ChenShunsuke Chiba
Jan 31, 2015·Organic Letters·Yasuhiro NishikawaOsamu Hara
Mar 20, 2018·Organic Letters·Hao YuCarsten Bolm
Feb 18, 2020·Chemical Reviews·Aaron TrowbridgeMatthew J Gaunt
Dec 3, 2014·Bioorganic & Medicinal Chemistry Letters·Andrea StevenazziMaria Lattanzio

❮ Previous
Next ❯

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.