Volume 27, Issue 16
Preparative Organic Chemistry
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ChemInform Abstract: Further Studies on the anti-Selective Aldol Reaction of Chiral Imides.

B. C. RAIMUNDO

B. C. RAIMUNDO

Dep. Chem., Univ. Calif., Berkeley, CA 94720, USA

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C. H. HEATHCOCK

C. H. HEATHCOCK

Dep. Chem., Univ. Calif., Berkeley, CA 94720, USA

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First published: April 16, 1996

Abstract

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ChemInform Abstract

During a study concerning the construction of the lankanolide framework, a synthetically useful boron-mediated anti-selective aldol condensation of the imide (I) with acetaldehyde (II) to give the desired synthon (III) (79% isolated yield) is reported. The method is complementary to existing Al-mediated processes. Additionally, tartaric acid is found to remove boron from the aldol condensation mixture without destruction of the aldolate.

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