Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids

Organic Letters
Rajeswari ThayumanavanCarlos F Barbas III

Abstract

[reaction: see text] A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using l-proline or (S)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives.

References

Oct 23, 2001·Angewandte Chemie·Peter I. Dalko, Lionel Moisan
Nov 9, 2001·Organic Letters·J M Betancort, C F Barbas
Jan 5, 2002·The Journal of Organic Chemistry·Armando CórdovaCarlos F Barbas
Feb 28, 2002·Journal of the American Chemical Society·Armando CórdovaCarlos F Barbas
Aug 29, 2002·Journal of the American Chemical Society·Leonard A McDonaldR Thomas Williamson
Sep 4, 2003·Journal of the American Chemical Society·Sean P BrownDavid W C MacMillan
Oct 16, 2003·Journal of the American Chemical Society·Tomotaka OkinoYoshiji Takemoto
Dec 6, 2003·The Journal of Organic Chemistry·Wolfgang NotzCarlos F Barbas
Mar 17, 2004·Angewandte Chemie·Takahiko AkiyamaKohei Fuchibe
Apr 1, 2004·Journal of the American Chemical Society·Michael P BrochuDavid W C MacMillan
Apr 7, 2004·Proceedings of the National Academy of Sciences of the United States of America·Scott E Denmark, Tommy Bui
Apr 7, 2004·Proceedings of the National Academy of Sciences of the United States of America·Norie MomiyamaHisashi Yamamoto
Apr 8, 2004·Proceedings of the National Academy of Sciences of the United States of America·Avinash N ThadaniViresh H Rawal
Apr 15, 2004·Journal of the American Chemical Society·Nis HallandKarl Anker Jørgensen
Apr 29, 2004·Journal of the American Chemical Society·Daisuke Uraguchi, Masahiro Terada
Jun 24, 2004·Angewandte Chemie·Suju P MathewDonna G Blackmond

❮ Previous
Next ❯

Citations

Jul 24, 2008·Chemical Society Reviews·Michelangelo GruttadauriaRenato Noto
Apr 27, 2010·Chemical Society Reviews·Barry M Trost, Cheyenne S Brindle
Jan 15, 2015·Chemical Communications : Chem Comm·Fernanda G FinelliRodrigo O M A de Souza
Dec 17, 2015·Chemistry : a European Journal·Sun Min KimJung Woon Yang
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Jun 22, 2018·Chemistry : a European Journal·Amparo Sanz-MarcoBelén Martín-Matute
Apr 1, 2015·Angewandte Chemie·Karin WeidnerMasakatsu Shibasaki
Feb 22, 2013·Chemistry : a European Journal·Huicai HuangJinxing Ye
Mar 29, 2014·Chemistry, an Asian Journal·Andrea GualandiPier Giorgio Cozzi
May 6, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sha-Sha KanTai-Ran Kan
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Apr 19, 2008·Angewandte Chemie·Alessandro Dondoni, Alessandro Massi
Sep 17, 2010·Chembiochem : a European Journal of Chemical Biology·Julia GavrilyukCarlos F Barbas
Feb 22, 2011·Chemistry : a European Journal·Marion BarbazangesPeter Turner
Jan 22, 2020·Angewandte Chemie·Connor J ThomsonDarren J Dixon
May 14, 2005·Angewandte Chemie·Derek D SteinerCarlos F Barbas
Nov 17, 2012·Chemical Society Reviews·José Alemán, Silvia Cabrera
Dec 13, 2007·Chemical Reviews·Santanu MukherjeeBenjamin List
Oct 22, 2008·Organic Letters·James P TellamDavid R Carbery
Jun 15, 2007·The Journal of Organic Chemistry·Tõnis KangerMargus Lopp
Aug 27, 2005·Organic Letters·Jeff T SuriCarlos F Barbas
Aug 27, 2005·Organic Letters·Auxiliadora PrietoKarl Anker Jørgensen
Oct 21, 2010·The Journal of Organic Chemistry·James P Tellam, David R Carbery
Oct 23, 2010·Organic Letters·Brinton Seashore-LudlowPeter Somfai
Feb 9, 2012·The Journal of Organic Chemistry·Ulf Scheffler, Rainer Mahrwald
Oct 18, 2011·Journal of the American Chemical Society·Taichi KanoKeiji Maruoka

❮ 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.