Archive for May, 2008

Published by admin on 18 May 2008

A Ring Size-Selective Reduction of Lactones Using SmI2 and H2O

The SmI2-H2O reducing system shows complete selectivity for six-membered lactones over other classes of lactone and esters:

Reduction of lactones with SmI2

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Published by admin on 17 May 2008

Efficient Synthesis of Ynamides

A copper-catalyzed method for the preparation has been identified.

Synthesis of ynamides

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Published by admin on 16 May 2008

Direct One-Pot Synthesis of Phenanthrenes via Suzuki-Miyaura Coupling/Aldol Condensation Cascade Reaction

One-pot cascade reaction of Suzuki-Miyaura coupling/aldol condensation can be a mild, simple, and efficient method for the synthesis of highly functionalized phenanthrenes.

Synthesis of Phenanthrenes

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Published by admin on 14 May 2008

A Multicomponent Synthesis of Imidazolones

The palladium-catalyzed four-component cross-coupling of imines, chloroformates, organostannane reagents, and carbon monoxide can be utilized to generate ketocarbamates (1), which are amenable to cyclization to generate imidazolones. Considering the mild conditions (1 atm of carbon monoxide, room temperature) and simple building blocks employed, this provides straightforward access to these heterocycles.

Synthesis of imidazolones

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Published by admin on 13 May 2008

Highly Chemoselective Metal-Free Reduction of Tertiary Amides

This communication describes the chemoselective metal-free reduction of tertiary amides to the corresponding amines.

Reduction of tertiary amides (with Hantzsch ester)

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Published by admin on 09 May 2008

Aromatics with a twist

In the 1930s, the physical chemist Erich Huckel predicted that annulenes containing 4n+2 mobile electrons should be stable (aromatic), and that those with 4n electrons should be unstable (antiaromatic) [1]. His prediction spurred a number of synthetic chemists to prepare these molecules. Each successful synthesis confirmed Huckel’s predictions. But in 1964, a spectacular theoretical prediction was made: the Huckel rules are reversed for annulenes with a 180° twist (so-called Mobius annulenes [2]). High-level theoretical calculations confirmed that Mobius rings with 4n electrons are indeed truly aromatic, whereas those with 4n+2 electrons are antiaromatic. Synthetic chemists once again rushed to prove the prediction experimentally, but all early attempts failed. It wasn’t until 2003 that the first synthesis of a Mobius annulene was achieved [3].

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Published by admin on 07 May 2008

Catalytic, PMe3-mediated conversion of secondary nitroalkanes to ketones: a very mild Nef-type process

Very mild catalytic variants of the reductive Nef-like reactions are disclosed.

Nef reaction

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Published by admin on 05 May 2008

One-pot terminal alkene homologation using a tandem olefin cross-metathesis/allylic carbonate reduction sequence

A one-carbon of terminal alkenes has been developed utilizing an olefin cross-metathesis followed by a palladium-mediated allylic carbonate reduction.

Homologation

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Published by admin on 03 May 2008

Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3

The combination of cheap and readily available sodium borohydride and a catalytic amount of RuCl3·H2O provides a method for the selective reduction of mono- and disubstituted olefins.

Reduction of olefins

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