𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Asymmetric Synthesis and Enantioselectivity of Binding of 1-Aryl-1,2,3,4-tetrahydroisoquinolines at the PCP Site of the NMDA Receptor Complex

✍ Scribed by Klaus Th. Wanner; Herbert Beer; Georg Höfner; Matthias Ludwig

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
444 KB
Volume
1998
Category
Article
ISSN
1434-193X

No coin nor oath required. For personal study only.

✦ Synopsis

A new method for the asymmetric synthesis of 1-substituted enantiomerically pure 11c-g and 12c-g (ee Ͼ 99 %), 1-aryltetrahydroisoquinolines, were evaluated for their affinity to tetrahydroisoquinolines is presented. It is based on stereoselective addition reactions of organometallic the PCP [1-(1-phenylcyclohexyl)piperidine] binding site of the NMDA (N-methyl D-aspartate) receptor. In each case the compounds to the intermediate N-acyliminium ion 6, which is provided with an N-acyl group as a chiral auxiliary. In enantiomers 11 exhibited a higher affinity than those of 12, with the potencies of the enantiomers differing by a factor of addition reactions with organomagnesium and organozinc reagents diastereoselectivities from 70:30 to 95:5 (for 7/8) 4 (11/12g) to 27 (11/12c). The absolute configuration of the more potent enantiomers 11 is in accordance with the were observed with the zinc reagents in general leading to markedly improved stereoselectivities. By catalytic stereochemical requirement found for FR 115427 (3) which is a close analogue. hydrogenation of 7 and 8 and after removal of the chiral auxiliary the target compounds 11 and 12 were obtained. The 7g: Colorless crystals, m.p. 215°C. Ϫ [α] D ϭ ϩ435 (c ϭ 1.105 in 6.99 (d,

📜 SIMILAR VOLUMES

ChemInform Abstract: Asymmetric Synthesi
ChemInform Abstract: Asymmetric Synthesis and Enantioselectivity of Binding of 1-Aryl-1,2,3,4-tetrahydroisoquinolines at the PCP Site of the NMDA Receptor Complex.
✍ K. TH. WANNER; H. BEER; G. HOEFNER; M. LUDWIG 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v