Deracemization of axially dissymmetric compounds by enantioselective dehydrohalogenation using chiral lithium amides -II-

✍ Scribed by Lucette Duhamel; Alain Ravard; Jean-Christophe Plaquevent

• Book ID: 103976890
• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 148 KB
• Volume: 1
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/0957-4166(90)90030-e

✦ Synopsis

New findings about deracemlzatlon of unsaturated carboxylic acids 1 by enantloselectlve dehydrohalogenatlon of prochlral species 2 by chiral lithium amides leading to axially dlssymmetric compounds wlth 80% e.e. are reported. The role of the structure of the prochiral hydrochlorinated intermediate is discussed. An example of axial to central chlrality transfer Is described. f & -2 1 Daring oar previous stadies about the use of chiral lithium amides in asymmetric syathesis1*2.we recently reported that this class of chiral bases can exert high asymmetric induction in enantioselective dehydrohalogenatioa of prochiral acids 2, leading to optically active acids 1 bearing a chiral axi@ t Scheme 1 ): 12 racemic Scheme 1 23 prochiral 12 (S) ee 82 %