Stereospecific Diaza-Cope Rearrangement Driven by Steric Strain

✍ Scribed by Hyunwoo Kim; Yen Nguyen; Alan J. Lough; Jik Chin

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 388 KB
• Volume: 120
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200801974

✦ Synopsis

Vögtle and Goldschmitt [1] were the first to use hydrogen bonds to drive diaza-Cope rearrangement reactions to completion over thirty years ago. Although many interesting publications on the topic have since appeared, [2] no other weak forces have been found to drive the rearrangement reaction to completion. The diaza-Cope rearrangement is useful for synthesizing a wide variety of chiral vicinal diamines (Scheme 1) [3] that may be valuable for the development of catalysts [4] and drugs. [2, 5] [3,3] Sigmatropic reactions,