A new chiral axis due to N(open-chain imide)Ar bond: Unexpected racemization effect of an acyl group

✍ Scribed by Kazuhiro Kondo; Hiroko Fujita; Tomoko Suzuki; Yasuoki Murakami

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 252 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01078-3

✦ Synopsis

The first example of optically active compound 3c which possesses axial chirality based on the N(open-chain imide)-Ar bond rotation, is described. Furthermore, a quite interesting result is also described, namely, that 3a bearing a bulky acyl group rather than a small one racemized more rapidly. To explain this phenomenon, ~3C NMR experiments and the reaction with benzylamine of 3a-d were undertaken. These preliminary results suggest that the t-BuCO-N bond in 3a which racemized easily, is more twisted, compared with the CO-N bonds in 3 b-d which were relatively stable to racemization, o 1999 Elsevier Science Ltd. All rights reserved.