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Asymmetric sequential Michael reaction: Synthesis of optically active bicyclo[2.2.2]octane derivatives

✍ Scribed by Hiroto Nagaoka; Kaoru Kobayashi; Toshiaki Okamura; Yasuji Yamada

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 243 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)96934-x

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✦ Synopsis

The sequential Michael reaction of (S)-4,5-di-O-isopropylidenepent-2enoate la and lb with lithium enolate 2 afforded diastereo-and enantioselec--tively bicyclo[2.2.2]octane 2 and 6 (or 51, respectively. The adducts were efficiently converted into both enantiomeric keto aldehydes c-j-7 and (+)-I. Bicyclo[2.2.2]octane derivatives are versatile synthetic intermediate in total synthesis of natural products with variety type of carbon skeleton.

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