Highly diastereoselective preparation of aldol products using new functionalized allylic aluminum reagents.
Chloro-substituted triethylsilyl enol ethers derived from cyclohexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereoselective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.
Department Chemie, Ludwig-Maximilians-Universität München , Butenandtstr. 5-13, 81377 München, Germany.
Zhi-Liang
ZL
Shen
Zhihua
Z
Peng
Chun-Ming
CM
Yang
Julian
J
Helberg
Peter
P
Mayer
Ilan
I
Marek
Paul
P
Knochel
D000535:Aluminum / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003512:Cyclohexanones; D004987:Ethers; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D017646:Organosilicon Compounds; D000535:Aluminum