MαNP acid, a powerful chiral molecular tool for preparation of enantiopure alcohols by resolution and determination of their absolute configurations by the 1H NMR anisotropy method

✍ Scribed by Yusuke Kasai; Hiromi Taji; Takuma Fujita; Yoko Yamamoto; Megumi Akagi; Akinori Sugio; Shunsuke Kuwahara; Masataka Watanabe; Nobuyuki Harada; Akio Ichikawa; Volker Schurig

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 618 KB
• Volume: 16
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20077

✦ Synopsis

Abstract

A novel methodology using a chiral molecular tool of MαNP acid (1), 2‐methoxy‐2‐(1‐naphthyl)propionic acid, useful for preparation of enantiopure secondary alcohols and determination of their absolute configurations by the ^1^H NMR anisotropy method was developed; racemic MαNP acid (1) was enantioresolved with (–)‐menthol, and the enantiopure MαNP acid (S)‐(+)‐(1) obtained was allowed to react with racemic alcohol, yielding a mixture of diastereomeric esters, which was clearly separated by HPLC on silica gel. By applying the sector rule of ^1^H NMR anisotropy effect, the absolute configuration of the first‐eluted MαNP ester was unambiguously determined. Solvolysis or reduction of the first‐eluted MαNP esters yielded enantiopure alcohols. Chirality 16:569–585, 2004. © 2004 Wiley‐Liss, Inc.