Asymmetric synthesis of 3,4-annulated cyclopentenones from cycloalkenyl ketones and vinyl carbamates by diastereoselective carbonyl addition/conrotatory 4 pi ring closure

1-Lithiated O-vinyl carbamates add with high induced diastereoselectivity onto enantiomerically pure cycloalk-1-enyl (1-dibenzylamino)alkyl ketones. Subsequent O-carbamoyl migration, followed by a torquoselective, antarafacial 4 pi ring closure, leads to homochiral 2-substituted bicyclo[n.3.0]alk-1-...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 14; pp. 2264 - 2270
Main Authors Siemer, Michael, Froehlich, Roland, Hoppe, Dieter
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.07.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHOXY-N-METHYLAMIDES
ORGANIC-SYNTHESIS
REAGENTS
cyclopentenones
CIS-PROLINE
torquoselectivity
asymmetric synthesis
PROSTAGLANDINS
carbanion
electrocyclic reaction
STEREOSELECTIVE-SYNTHESIS
(Z)-ALKENE
LITHIATION
CYCLOPENTANNELATION
ALLENOLATE
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Summary:1-Lithiated O-vinyl carbamates add with high induced diastereoselectivity onto enantiomerically pure cycloalk-1-enyl (1-dibenzylamino)alkyl ketones. Subsequent O-carbamoyl migration, followed by a torquoselective, antarafacial 4 pi ring closure, leads to homochiral 2-substituted bicyclo[n.3.0]alk-1-ene-2-ones.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2008-1067150