153833-65-9Relevant academic research and scientific papers
Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry
Zaed, Ahmed M.,Grafton, Mark W.,Ahmad, Sajjad,Sutherland, Andrew
, p. 1511 - 1515 (2014)
A highly efficient one-pot multistep process involving an asymmetric Pd(II)-catalyzed Overman rearrangement and a Ru(II)-catalyzed ring-closing metathesis reaction has been developed for the preparation of (R)- or (S)-aminocyclopenta-2-enes. The rapid strategy employed and the relatively mild conditions of the one-pot process allowed the multigram synthesis of the carbocycles in high enantiomeric excess (92% ee). The synthetic utility of these compounds was demonstrated by the stereoselective incorporation of hydroxyl groups, generating cis-4- and cis-5-aminocyclopenta-2-en-1-ols, important building blocks for medicinal chemistry.
PCSK9 INHIBITORS AND METHODS OF USE THEREOF
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, (2020/07/31)
The invention relates to a novel inhibitor pharmacophore of PCSK9 and heteroaryl compounds that bind the PCSK9 protein.
PCSK9 INHIBITORS AND METHODS OF USE THEREOF
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, (2020/07/31)
The invention relates to novel heteroaryl compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cardiovascular diseases, and methods treating sepsis or septic shock, using the novel heterocyclic compounds disclosed herein.
On the α-lithiation-rearrangement of N-toluensulfonyl aziridines: Mechanistic and synthetic aspects
O'Brien, Peter,Rosser, Clare M.,Caine, Darren
, p. 9779 - 9791 (2007/10/03)
A detailed study of the rearrangement of five cycloalkene N-toluenesulfonyl (tosyl) aziridines using sec-butyllithium (with and without added ligands such as (-)-sparteine and TMEDA) has been carried out. Allylic sulfonamides were the main products from the cyclopentene and cyclohexene aziridines whereas bicyclic sulfonamides were obtained from the cycloheptene and cyclooctene aziridines. In most cases, p-toluenesulfonamide (TsNH 2) was produced as a by-product and a mechanistic explanation for its formation is forwarded. These reactions are believed to involve α-lithiation to a lithiated aziridine which can then partition through two pathways: (i) rearrangement to allylic or bicyclic sulfonamides via C-H insertion reactions or (ii) reductive alkylation to alkenes via attack by sec-butyllithium and subsequent elimination of TsNH2. In the (-)-sparteine reactions, the products were generated with 38-66% ee and the sense of asymmetric induction involved lithiation of the S-aziridine stereocentre. This is opposite to that observed with epoxides.
Asymmetric Catalysis by Vitamin B12: The Isomerization of Achiral Aziridines to Optically Active Allylic Amines
Zhang, Zhong da,Scheffold, Rolf
, p. 2602 - 2615 (2007/10/02)
Achiral N-acylaziridines are isomerized to optically active N-acyl-allylamines in ee's of up to 95percent by catalytic amounts of cob(I)alamin in MeOH.
