DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SUBSTITUTION-REACTIONS OF AN ISOINDOLINE-BORANE COMPLEX

Authors
BLAKE AJ EBDEN MR FOX DNA LI WS SIMPKINS NS
Citation
Aj. Blake et al., DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SUBSTITUTION-REACTIONS OF AN ISOINDOLINE-BORANE COMPLEX, Synlett, (2), 1998, pp. 189
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
2
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):2<189:DAESOA>2.0.ZU;2-Y
Abstract
The alkylation of N-methylisoindoline-borane complex is diastereoselec tive, the substitution occurring predominantly syn to the borane group . Use of the (BuLi)-Bu-S-sparteine reagent mixture enables the reactio n to be conducted enantioselectively, giving the chiral isoindoline-bo rane complexes in up to 89% ee. Both the relative and absolute configu rations of the alkylation products were established by X-ray structure determinations.