ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Sterochemistry of Ephedrine-like Compounds. - Absolute Configuration of the Four Isomeric cis- and trans-6-Amino-6,7,8,9-tetrahydro-5H-benzocycloheptenols-(5)Maintaining its absolute configuration, (+)-(S)-glutaminic acid is converted to (+)-(6S)-6-phthalimido-6,7,8,9-tetrahydro-5H-benzocycloheptenone-(5) (6a), which is also synthesized from (-)-(5R,6S)- or (+)-(5S,6S)-6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptenol-(5) (1a or b) under retention. The same mechanism is valid in the preparation of (-)-(6R)-6-phthalimido-6,7,8,9-tetrahydro-5H-benzocycloheptenone-(5) (6b) from (-)-(5R,6R)-6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptenol-(5) (1c). - The absolute configurations of all the four isomeric 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptenols-(5) (1a-d) are thus unambiguously determined.
Notes:
(+)-(S)-Glutaminsäure wird unter Erhaltung ihrer absoluten Konfiguration in (+)-(6S)-6-Phthalimido-6.7.8.9-tetrahydro-5H-benzocycloheptenon-(5) (6a) umgewandelt, das seinerseits ebenfalls unter Retention aus (-)-(5R.6S)- oder (+)-(5S.6S)-6-Amino-6.7.8.9-tetrahydro-5H-benzocycloheptenol-(5) (1a bzw. b) herstellbar ist. Entsprechendes gilt für die aus (-)-(5R.6R)-6-Amino-6.7.8.9-tetrahydro-5H-benzocycloheptenol-(5) (1c). - Damit sind die absoluten Konfigurationen aller vier isomeren 6-Amino-6.7.8.9-tetrahydro-5H-benzocycloheptenole-(5) (1a-d) eindeutig festgelegt.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.19727560110
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