Asymmetric Synthesis of a New Salen Type-titanium Complex as the Catalyst for Asymmetric Trimethylsilylcyanation of Aldehydes

This work describes the asymmetric synthesis of a new salen-type ligand via a Diels-Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destro...

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Bibliographic Details
Published inJournal of the Chinese Chemical Society (Taipei) Vol. 57; no. 4A; pp. 726 - 737
Main Authors Lin, Zheng-Chang, Chen, Chinpiao
Format Journal Article
LanguageEnglish
Published TAIPEI Chinese Chemical Soc 01.08.2010
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DOUBLE-ACTIVATION METHOD
Curtius rearrangement
Trimethylsilylcyanation
AROMATIC-ALDEHYDES
HIGH OPTICAL PURITY
ALPHA-ALKOXY ALDEHYDES
ENANTIOSELECTIVE CYANOSILYLATION
Asymmetric synthesis
CHEMOENZYMATIC SYNTHESIS
HYDROGEN-CYANIDE
AMINO ALDEHYDES
Diels-Alder reaction
CHIRAL LEWIS-ACID
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Summary:This work describes the asymmetric synthesis of a new salen-type ligand via a Diels-Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destroy this rigidity, and the eanatioselectivity was thereby increased to 85%ee.
ISSN:0009-4536
DOI:10.1002/jccs.201000101