From central to planar chirality, the first example of atropenantioselective cycloetherification

Using chiral quaternary ammonium hydroxide as base, cycloetherification of a linear achiral diarylheptanoid compd., by way of an intramol. SNAr reaction, provides corresponding enantiomerically enriched cyclophane in good to excellent yield. [on SciFinder (R)]


Published in:
Organic & Biomolecular Chemistry, 1, 1, 30-32
Year:
2003
Keywords:
Note:
CAN 139:69138
27-21
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1477-0520
written in English.
550349-81-0P; 550349-82-1P; 550349-83-2P Role: SPN (Synthetic preparation), PREP (Preparation) (atrop-isomer; prepn. of enantiomeric cyclophane derivs. via atropenantioselective cycloetherification of linear achiral diarylheptanoid compd. in presence of various chiral quaternary ammonium compd. bases); 549507-99-5; 550349-80-9 Role: CAT (Catalyst use), USES (Uses) (prepn. of enantiomeric cyclophane derivs. via atropenantioselective cycloetherification of linear achiral diarylheptanoid compd. in presence of various chiral quaternary ammonium compd. bases); 148595-92-0 Role: CAT (Catalyst use), RCT (Reactant), USES (Uses), RACT (Reactant or reagent) (prepn. of enantiomeric cyclophane derivs. via atropenantioselective cycloetherification of linear achiral diarylheptanoid compd. in presence of various chiral quaternary ammonium compd. bases); 148595-91-9P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of enantiomeric cyclophane derivs. via atropenantioselective cycloetherification of linear achiral diarylheptanoid compd. in presence of various chiral quaternary ammonium compd. bases); 118-10-5 (Cinchonine); 269733-58-6; 549507-98-4 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of enantiomeric cyclophane derivs. via atropenantioselective cycloetherification of linear achiral diarylheptanoid compd. in presence of various chiral quaternary ammonium compd. bases); 269733-59-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of enantiomeric cyclophane derivs. via atropenantioselective cycloetherification of linear achiral diarylheptanoid compd. in presence of various chiral quaternary ammonium compd. bases)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)