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Synthesis and Isolation of a Monoamine Having a Thermodynamically Stabilized Pseudo-chirotopic Nitrogen by Yuka Kobayashi; Kentaro Sano; Kazuhiko Saigo is a Chemistry article available to read on EtoBox.

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We have synthesized a tricyclic monoamine, (1S,4R)-(E)-7,3 0 -heptenylene-2,3:5,6-dibenzo-7-azabicyclo[2.2.1]heptane (1), by applying a ring-closing metathesis reaction in the key step of the synthetic route and by using preparative chiral HPLC for the separation. The X-ray crystallographic analysis of its salt with (1R)-camphor-10-sulfonic acid showed that the geometry and absolute configuration are (E) and (1S,4R), respectively. The theoretical calculations revealed that the inversion of the nitrogen atom at the 7-position of (1S,4R)-(E)-1 thus isolated takes place through a very slow process and that the configuration of the N( 7) is highly biased to (R), indicating that (1S,4R)-(E)-1 is a thermodynamically controlled N-pseudo-chirotopic compound ((1S,4R,7R)

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Author

Yuka Kobayashi; Kentaro Sano; Kazuhiko Saigo

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)