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Mild and Highly Enantioselective Vinylogous Aldol Reaction of Brassard's Diene with Aromatic Aldehydes by Combined Lewis Acid Catalyst

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Indexed by:期刊论文

Date of Publication:2010-08-06

Journal:JOURNAL OF ORGANIC CHEMISTRY

Included Journals:SCIE、EI、PubMed

Volume:75

Issue:15

Page Number:5326-5329

ISSN No.:0022-3263

Abstract:The combined Lewis acid catalytic system, generated from (R)-1,1'-bi-2-naphthol [(R)-BINOL], Ti(O-i-Pr)(4), H2O, and lithium chloride, effectively catalyzed the enantioselective vinylogous aldol reaction of Brassard's diene with aromatic aldehydes affording the (Z)-delta-hydroxyl-alpha,beta-unsaturated esters exclusively in good yields with excellent enantioselectivities (90-99% ee) under mild conditions. A Lewis acid Lewis acid bifunctional working model was proposed for the catalytic process based on some control experiments.

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