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Stereochemistry of cycloadducts from 3,4‐dihydro‐6,7‐dimethoxyisoquinoline ylide and olefins
Author(s) -
Janke Frank,
Himmelreich Uwe,
Tóth Gábor,
Tischer Thomas,
Kádas István,
Bende Zoltán,
Töke László
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280406
Subject(s) - ylide , chemistry , olefin fiber , cycloaddition , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , catalysis
Cycloaddition of 2‐methoxycarbonylmethyl‐3,4‐dihydro‐6,7‐dimethoxyisoquinolinium ylide with various E ‐substituted olefin type dipolarophiles gave products of 10b‐H, 1‐H, 2‐H and 3‐H α,α,β,β ‐relative configuration with one exception. Relative configuration of compounds prepared has been determined by 1D and 2D 1 H and 13 C nmr techniques. It has also been detected that a triple trans ⇌ cis‐1 ⇌ cis ‐2 conformation equilibrium exists in solution.