TY - JOUR
T1 - Synthesis and absolute structure determination of camphanoate derivatives of five bicyclo[3.1.0]hexane compounds
AU - Krief, A.
AU - Ollevier, T.
AU - Swinnen, D.
AU - Norberg, B.
AU - Baudoux, G.
AU - Evrard, G.
N1 - Copyright 2006 Elsevier B.V., All rights reserved.
PY - 1998/1/1
Y1 - 1998/1/1
N2 - 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
AB - 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
UR - http://www.scopus.com/inward/record.url?scp=0032027135&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0032027135
SN - 0108-2701
VL - 54
SP - 392
EP - 398
JO - Acta crystallographica. Section C: Crystal structure communications
JF - Acta crystallographica. Section C: Crystal structure communications
IS - 3
ER -