Synthesis and absolute structure determination of camphanoate derivatives of five bicyclo[3.1.0]hexane compounds

A. Krief, T. Ollevier, D. Swinnen, B. Norberg, G. Baudoux, G. Evrard

Research output: Contribution to journalArticlepeer-review

Abstract

The relative and absolute stereochemistry of five compounds, (1R,2S,4R,5S)-exo-2-acetoxy-3,3-dimethylbicyclo[3.1.0]hexan-exo-4-yl camphanoate, CHO, (I), (1R,2S,4R,5S,6R)-exo-2-acetoxy-3,3,exo-6-trimethylbicyclo[3.1.0]hexan-exo-4-yl camphanoate, CHO, (II), (1R,2S,4R,5S,6S)-exo-2-acetoxy-3,3,endo-6-trimethylbicyclo[3.1.0]hexan-exo-4-yl camphanoate, CH-O, (III), (1S,2S,4R,5R,6S)-exo-2-acetoxy-endo-6-(3-butenyl)-3,3,exo-6-trimethylbicyclo[3. 1.0]hexan-exo-4-yl camphanoate, CHO, (IV), and (1S,2S,4R,5R,6S)-endo-2-acetoxy-3,3,exo-6-trimethylbicyclo[3.1.0]hexanendo-4-yl camphanoate, CHO, (V), (camphanoate is 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate) have been determined and the conformation of the five-membered ring of each one is discussed. These compounds were synthesized by an enantioselective esterase-catalysed hydrolysis followed by acylation with camphanoyl chloride
Original languageEnglish
Pages (from-to)392-398
Number of pages7
JournalActa crystallographica Section C: Crystal Structure communications
Volume54
Issue number3
Publication statusPublished - 1 Jan 1998

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