Thursday 10 July 2014

Buckyball boron

The stability of the predicted boron cage stems from its unique structural geometry
Since C₆₀ fullerene’s discovery in 1985 and the subsequent Nobel prize awarded to Robert Curl, Harry Kroto and Richard Smalley in 1996, researchers have been challenging themselves to make similar structures with other elements in the hope of finding exciting alternative nano building blocks.
http://www.rsc.org/chemistryworld/2014/07/boron-cage-b38-fullerene

Thursday 26 June 2014

Acid-Facilitated Debenzylation of N-Boc, N-Benzyl Double Protected 2-Aminopyridinomethylpyrrolidine Derivatives

Tetrahedron. Author manuscript; available in PMC Feb 4, 2013.

Published in final edited form as:

Tetrahedron. Feb 4, 2012; 68(5): 1359–1366.

Published online Dec 13, 2011. doi: 10.1016/j.tet.2011.12.013

PMCID: PMC3358821

NIHMSID: NIHMS344972

Acid-Facilitated Debenzylation of N-Boc, N-Benzyl Double Protected 2-Aminopyridinomethylpyrrolidine Derivatives

Haitao Ji,^1,² Qing Jing,¹ Jinwen Huang,^1,³ and Richard B. Silverman^1,^*

Author information ► Copyright and License information ►

The publisher's final edited version of this article is available at Tetrahedron

Abstract

2-Aminopyridinomethyl pyrrolidines represent a class of highly potent and selective neuronal nitric oxide synthase inhibitors. Conditions for a Mitsunobu reaction of a naphthol and a hindered secondary alcohol were optimized to give good to excellent yields. A key step in the synthesis of these inhibitors is the deprotection of the benzyl group from the N-Boc and N-Bn double protected 2-aminopyridine ring at a late stage of the synthesis, which has been proven difficult in our previous syntheses. Acetic acid was found to facilitate the N-Bn deprotection.

Keywords: 2-Aminopyridinomethyl pyrrolidines, Mitsunobu reaction, N-Benzyl deprotection, Palladium-catalyzed hydrogenation