Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Notes
A Chiral Ligand-Mediated Asymmetric Addition of a Lithium BHA Ester Enolate to an Aldehyde
Yumiko NomuraMayu IguchiHirohisa DoiKiyoshi Tomioka
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2002 年 50 巻 8 号 p. 1131-1134

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The asymmetric reaction of a lithium enolate generated from a BHA (2, 6-di-tert-buty-4-methoxyphenyl) propanoate was allowed to react with benzaldehyde in the presence of a diether-type chiral ligand affording the corresponding anti-aldol product in a moderate enantioselectivity. A tetradentate ligand induced better enantioselectivity albeit relative loss of anti-selectivity. A variation of lithiating amide agent affected the selectivity, indicating involvement of an amine as a component of the mixed aggregate. Absolute configuration of some of the aldol products was determined by standard transformations.
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© 2002 The Pharmaceutical Society of Japan
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