Latest Articles of Tetrahedron


Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides 10.1016/j.tet.2018.03.003 2018-04-11 A DMEDA-promoted and copper-catalyzed approach has been designed for the coupling of aryl halides and chiral α-aminoamides to afford a range of functionalized chiral α-amino anilides. This method has a higher yield and better reproducibility than those under ...
A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs 10.1016/j.tet.2018.04.022 2018-04-11 Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde i...
Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin 10.1016/j.tet.2018.02.051 2018-04-10 Kosugi-Migita-Stille cross coupling reactions of (ethenyl)tributyltin with all isomeric permutations of bromophenyl triflate and bromo-nitrophenyl triflate were examined in order to determine the chemoselectivity of carbon-bromine versus carbon-triflate bond ...
Process design methodology for organometallic chemistry in continuous flow systems 10.1016/j.tet.2018.04.020 2018-04-07 This publication summarises the methodology applied in the process design and scale up of fast, exothermic reactions using organometallic reagents for synthesis of intermediates in the production of Active Pharmaceutical Ingredient (API). Process understandin...
Substrate engineering: Effects of different N-protecting groups in the CAL-B-catalysed asymmetric O-acylation of 1-hydroxymethyl-tetrahydro-β-carbolines 10.1016/j.tet.2018.04.012 2018-04-07 In the frame of substrate engineering, the steric effect of different N-protecting groups on the enantioselectivity and reaction rate of CAL-B-catalysed (S)-selective O-acylation of N-protected 1-hydroxymethyl-tetrahydro-β-carbolines was investigated. Excelle...
Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles 10.1016/j.tet.2018.04.017 2018-04-07 Highly functionalized pyrroles with appropriate regiochemical functionality represent an important class of marine natural products and potential drug candidates. We describe herein a detailed study of the reaction of α-aminoacid esters with vinylogous amides...
Total Synthesis of Sch 725674 10.1016/j.tet.2018.04.014 2018-04-06 A concise total synthesis of the macrolactone natural product Sch 725674 is accomplished starting from commercially available 2-deoxy-d-ribose. Pivotal reactions employed in the synthesis include the addition of 4-pentenylmagnesium bromide to the lactol deriv...
An efficient synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines and application in cyclisation reactions 10.1016/j.tet.2018.03.075 2018-04-03 The synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines (nitrodienamines) from 3-aminocrotonates and nitroacetaldehyde potassium salt, has been performed in 45–89% yields. This one-step protocol works efficiently with a broad range of N-H and N-substi...
Synthesis of N-Sulfonylformamidines by tert-butyl Hydroperoxide–Promoted, metal-free, direct oxidative dehydrogenation of aliphatic amines 10.1016/j.tet.2018.03.074 2018-04-03 A direct and convenient metal-free method to prepare sulfonyl amidines in the presence of aqueous tert-butyl hydroperoxide (T-HYDRO) has been developed. Different tertiary and secondary amines were tested for compatibility with the oxidative conditions and co...
Direct enolization chemistry of 7-azaindoline amides: A case study of bis(tetrahydrophosphole)-type ligands 10.1016/j.tet.2018.03.073 2018-03-31 7-Azaindoline amides are particularly useful in direct enolization chemistry due to their facilitated enolization in soft Lewis acid/Brønsted base cooperative catalysis. The Cu(I) complex of (R,R)-Ph-BPE, a bis(tetrahydrophosphole)-type chiral bisphosphine li...

Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides

10.1016/j.tet.2018.03.003

2018-04-11

A DMEDA-promoted and copper-catalyzed approach has been designed for the coupling of aryl halides and chiral α-aminoamides to afford a range of functionalized chiral α-amino anilides. This method has a higher yield and better reproducibility than those under ...

A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

10.1016/j.tet.2018.04.022

2018-04-11

Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde i...

Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin

10.1016/j.tet.2018.02.051

2018-04-10

Kosugi-Migita-Stille cross coupling reactions of (ethenyl)tributyltin with all isomeric permutations of bromophenyl triflate and bromo-nitrophenyl triflate were examined in order to determine the chemoselectivity of carbon-bromine versus carbon-triflate bond ...

Process design methodology for organometallic chemistry in continuous flow systems

10.1016/j.tet.2018.04.020

2018-04-07

This publication summarises the methodology applied in the process design and scale up of fast, exothermic reactions using organometallic reagents for synthesis of intermediates in the production of Active Pharmaceutical Ingredient (API). Process understandin...

Substrate engineering: Effects of different N-protecting groups in the CAL-B-catalysed asymmetric O-acylation of 1-hydroxymethyl-tetrahydro-β-carbolines

10.1016/j.tet.2018.04.012

2018-04-07

In the frame of substrate engineering, the steric effect of different N-protecting groups on the enantioselectivity and reaction rate of CAL-B-catalysed (S)-selective O-acylation of N-protected 1-hydroxymethyl-tetrahydro-β-carbolines was investigated. Excelle...

Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles

10.1016/j.tet.2018.04.017

2018-04-07

Highly functionalized pyrroles with appropriate regiochemical functionality represent an important class of marine natural products and potential drug candidates. We describe herein a detailed study of the reaction of α-aminoacid esters with vinylogous amides...

Total Synthesis of Sch 725674

10.1016/j.tet.2018.04.014

2018-04-06

A concise total synthesis of the macrolactone natural product Sch 725674 is accomplished starting from commercially available 2-deoxy-d-ribose. Pivotal reactions employed in the synthesis include the addition of 4-pentenylmagnesium bromide to the lactol deriv...

An efficient synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines and application in cyclisation reactions

10.1016/j.tet.2018.03.075

2018-04-03

The synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines (nitrodienamines) from 3-aminocrotonates and nitroacetaldehyde potassium salt, has been performed in 45–89% yields. This one-step protocol works efficiently with a broad range of N-H and N-substi...

Synthesis of N-Sulfonylformamidines by tert-butyl Hydroperoxide–Promoted, metal-free, direct oxidative dehydrogenation of aliphatic amines

10.1016/j.tet.2018.03.074

2018-04-03

A direct and convenient metal-free method to prepare sulfonyl amidines in the presence of aqueous tert-butyl hydroperoxide (T-HYDRO) has been developed. Different tertiary and secondary amines were tested for compatibility with the oxidative conditions and co...

Direct enolization chemistry of 7-azaindoline amides: A case study of bis(tetrahydrophosphole)-type ligands

10.1016/j.tet.2018.03.073

2018-03-31

7-Azaindoline amides are particularly useful in direct enolization chemistry due to their facilitated enolization in soft Lewis acid/Brønsted base cooperative catalysis. The Cu(I) complex of (R,R)-Ph-BPE, a bis(tetrahydrophosphole)-type chiral bisphosphine li...