- A chiral synthesis of (-)-spiro[1-azabicyclo[2.2.2]octane-3,5′- oxazolidin-2′-one]: A conformationally restricted analogue of acetylcholine that is a potent and selective α7 nicotinic receptor agonist
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A direct, short chiral synthesis of the selective α7 nicotinic receptor agonist (-)-spiro[1-azabicyclo[2.2.2]-octane-3,5′-oxazolidin- 2′-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.
- Macor, John E.,Mullen, George,Verhoest, Patrick,Sampognaro, Anthony,Shepardson, Bruce,Mack, Robert A.
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p. 6493 - 6495
(2007/10/03)
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- Stereoselective Aldol Reactions with (R)- and (S)-2-Hydroxy-1,2,2-triphenylethyl Acetate and Related Glycol Monoacetates
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The enolate 7a, formed by double deprotonation of the ester 5a, is added to aldehydes.The influences of the enolate gegenion, of the solvent, and of the reaction temperature on the ratio of the isomeric products 9:10 are studied.The highest degrees of dia
- Devant, Ralf,Mahler, Ulrike,Braun, Manfred
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p. 397 - 406
(2007/10/02)
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- (R)- AND (S)-2-ACETOXY-1,1,2-TRIPHENYLETHANOL - EFFECTIVE SYNTHETIC EQUIVALENTS OF A CHIRAL ACETATE ENOLATE
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The enolate 3, easily available by double deprotonation of (R)-2-acetoxy-1,1,2-triphenylethanol (5), adds in a highly stereoselective manner to aldehides.Hydrolysis of the adducts 6/7 affods the acids 2.
- Braun, Manfred,Devant, Ralf
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p. 5031 - 5034
(2007/10/02)
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