Aza-Wittig Rearrangements of N-Benzyl and N-Allyl Glycine Methyl Esters. Discovery of a Surprising Cascade Aza-Wittig Rearrangement/Hydroboration Reaction

The Journal of Organic Chemistry
Renata K Everett, John P Wolfe

Abstract

Treatment of N-(arylmethyl)-N-aryl or N-allyl-N-aryl glycine methyl ester derivatives with (n)Bu2BOTf and (i)Pr2NEt effects an aza-Wittig rearrangement that provides N-aryl phenylalanine methyl ester derivatives and N-aryl allylglycine methyl ester derivatives, respectively, in good yield with moderate to good diastereoselectivity. Under similar conditions, analogous substrates bearing N-carbonyl groups are converted to 1,4,2-oxazaborole derivatives. Additionally, N-allyl-N-aryl glycine methyl ester derivatives subjected to similar conditions at elevated temperatures undergo an aza-[2,3]-Wittig rearrangement, followed by a subsequent hydroboration oxidation reaction, to afford substituted amino alcohol products.

References

Jan 10, 2001·The Journal of Organic Chemistry·J C AndersonM E Swarbrick
Dec 4, 2003·Bioorganic & Medicinal Chemistry Letters·Brent R StranixJocelyn Yelle
Apr 24, 2004·The Journal of Organic Chemistry·Jan BlidPeter Somfai
Jun 30, 2005·Journal of the American Chemical Society·Jan BlidPeter Somfai
Sep 22, 2006·Organic Letters·Myra Beaudoin Bertrand, John P Wolfe
Jul 16, 2008·Accounts of Chemical Research·Ruben Martin, Stephen L Buchwald
Aug 15, 2009·Journal of the American Chemical Society·Natalie C GiampietroJohn P Wolfe
Mar 17, 2010·Angewandte Chemie·Natalie C Giampietro, John P Wolfe
Jan 10, 2012·Chemistry : a European Journal·Bao-Hua XuGerhard Erker
Mar 26, 2013·Organic Letters·Shunsuke Sueki, Yoichiro Kuninobu
Jun 1, 2013·The Journal of Organic Chemistry·François Brucelle, Philippe Renaud
Jun 20, 2013·Angewandte Chemie·Alastair J J Lennox, Guy C Lloyd-Jones
Oct 5, 2013·Chemical Society Reviews·Alastair J J Lennox, Guy C Lloyd-Jones
Sep 18, 2014·Journal of the American Chemical Society·Iván SorribesMatthias Beller

❮ Previous
Next ❯

Citations

Sep 16, 2016·Organic Letters·Juan ZhangShi-Kai Tian
Oct 14, 2016·Organic Letters·Tony RoyAkkattu T Biju
Aug 9, 2016·Chemical Communications : Chem Comm·Eiji TayamaYuka Toma
Jan 31, 2020·Chirality·Nobuki KatoMinoru Ueda

❮ 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.

© 2021 Meta ULC. All rights reserved