TY - JOUR
T1 - Indium-mediated regio- and diastereoselective reduction of norbornyl α-diketones
AU - Khan, Faiz Ahmed
AU - Dash, Jyotirmayee
AU - Sudheer, Ch
PY - 2004/5/17
Y1 - 2004/5/17
N2 - A novel, efficient, and regio-as well as diastereoselective conversion of non-enolizable bicyclic α-diketones into synthetically useful acyloins mediated by indium metal is described. The reduction is highly diastereoselective, leading exclusively to endo-acyloins, (endo-hydroxyl groups) in excellent yields, and tolerates a variety of sensitive substituents, such as acetate, ester, and bridgehead halogens. The regioselectivity in the reductions of monosubstituted α-diketones varied from 70:30 to 100:0 for the two possible isomeric alcohols. The methodology is extended to the synthesis of highly functionalized cyclopentane carboxaldehydes, potential building blocks in organic syntheses, by cleavage of the acyloins by treating them with Pb(OAc)4 in MeOH/PhH. Allylindium additions to carboxaldehydes 22 have been found to be highly diastereoselective.
AB - A novel, efficient, and regio-as well as diastereoselective conversion of non-enolizable bicyclic α-diketones into synthetically useful acyloins mediated by indium metal is described. The reduction is highly diastereoselective, leading exclusively to endo-acyloins, (endo-hydroxyl groups) in excellent yields, and tolerates a variety of sensitive substituents, such as acetate, ester, and bridgehead halogens. The regioselectivity in the reductions of monosubstituted α-diketones varied from 70:30 to 100:0 for the two possible isomeric alcohols. The methodology is extended to the synthesis of highly functionalized cyclopentane carboxaldehydes, potential building blocks in organic syntheses, by cleavage of the acyloins by treating them with Pb(OAc)4 in MeOH/PhH. Allylindium additions to carboxaldehydes 22 have been found to be highly diastereoselective.
KW - Diastereoselectivity
KW - Diketones
KW - Indium
KW - Reduction
KW - Regioselectivity
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U2 - 10.1002/chem.200305656
DO - 10.1002/chem.200305656
M3 - Article
C2 - 15146523
AN - SCOPUS:2942579789
SN - 0947-6539
VL - 10
SP - 2507
EP - 2519
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 10
ER -