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The stereoselectivity of michael additions leading to enantiomerically pure indoloquinolizidones

✍ Scribed by Peng, Shiqi ;Winterfeldt, Ekkehard

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 443 KB
Volume: 1990
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199019900160

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✦ Synopsis

Abstract

Acylation of the carboline derivatives 6 and 9 with diketene affords the corresponding N‐(acetoacetyl)carbolines 7 and 10, respectively. While 10 can be converted into a 1:2.1 mixture of the title compounds 11 a and 11 b on treatment with oxalic acid, the cyclic acetal 7 can only be cyclized to yield the pyridone derivative 8. Michael addition of methyl malonate to the unsaturated ketone 11 b proceeds with excellent stereoselectivity to generate the keto diester 12 a which, on treatment with a base is transformed into its diastereoisomer 12 b. In contrast to 11 b, its stereoisomer 11 a does not react with methyl malonate.

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