1,7-induction of chirality in Mukaiyama aldol reactions using pi-allyltricarbonyliron lactone and lactam complexes as chiral templates

The Mukaiyama aldol reactions of silyl enol ether-substituted pi-allyltrica rbonyliron lactone and lactam complexes with aldehydes under BF3. OEt2 acti vation proceed with moderate to excellent diastereocontrol. The level of di astereocontrol is strongly affected by the nature of the endo substituent o n the complex, seven carbon atoms distant from the reaction site. A detaile d investigation of the reaction is presented and a model for the observed s tereoselectivity proposed. (C) 1999 Elsevier Science Ltd. All rights reserv ed.