Facile Synthesis of ( S,S )‐1,2‐Diacylamides and ( S,S )‐1,2‐Diamines with C 2 ‐Symmetry

Authors: Ai, Lin¹; Xiao, Jichuan¹; Wang, Guo¹; Shen, Xiumin¹; Zhang, Cong¹

Source: Synthetic Communications, Volume 36, Number 19, 2006 , pp. 2859-2875(17)

Publisher: Taylor and Francis Ltd

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Abstract:

A series of chiral vicinal tertiary diacylamides with C 2 ‐symmetry was synthesized from ( S )‐α‐phenylethylamine, different aromatic aldehydes, and oxalyl chloride. The diacylamides obtained were then reduced to afford chiral vicinal diamines with C 2 ‐symmetry. We propose that the diacylamides existed in four stable conformational isomers in solution because of the dihedral angle between acylamide bonds.

Keywords: ( S , S )‐1,2‐Diacylamides; ( S , S )‐1,2‐diamines; C 2 ‐symmetry; synthesis

Document Type: Research article

DOI: 10.1080/00397910600770698

Affiliations: 1: Department of Chemistry, Beijing Normal University, Beijing, China

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