Synthesis of Enantiomerically and Diastereomerically Pure Cyclopentanols by asymmetric Cyclocarbolithiation of 5-Alkenyl Carbamates

Synthesis of Enantiomerically and Diastereomerically Pure Cyclopentanols by asymmetric Cyclocarbolithiation of 5-Alkenyl Carbamates

Three vicinal stereocenters are formed in the (−)‐sparteine‐induced cyclobolithiation of 6‐phenyl‐5‐hexenyl carbamates. The anionic cyclization products can be trapped with various electrophiles (El) to provide enantiomerically pure cyclopentanol derivatives [Eq. (a); Cby = 2,2,4,4‐tetramethyl‐1,3‐o...

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Veröffentlicht in:Angewandte Chemie International Edition 1997-09, Vol.36 (16), p.1764-1766
Hauptverfasser: Woltering, Michael J., Fröhlich, Roland, Hoppe, Dieter
Format: Artikel
Sprache:eng
Schlagworte:
(−)-sparteine
asymmetric synthesis
carbanions
carbolithiations
cyclopentatnols
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Zusammenfassung:Three vicinal stereocenters are formed in the (−)‐sparteine‐induced cyclobolithiation of 6‐phenyl‐5‐hexenyl carbamates. The anionic cyclization products can be trapped with various electrophiles (El) to provide enantiomerically pure cyclopentanol derivatives [Eq. (a); Cby = 2,2,4,4‐tetramethyl‐1,3‐oxazolidin‐3‐carboxylate].
ISSN:0570-0833
1521-3773
DOI:10.1002/anie.199717641