Catalytic addition of alkenylzirconocene chloride to 3,4-dihydroisoquinoline and its enantioselective reaction

The addition of alkenylzirconocene chloride to 3,4-dihydroisoquinoline in the presence of a stoichiometric amount of acylating agent such as (Boc) 2O or ClCOOC 2H 5 was carried out in the presence of a catalytic amount of Cu(I) (10 mol %) to give an alkenylation–carbamation product. The enantioselec...

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Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 5; pp. 587 - 589
Main Authors Saito, Akio, Iimura, Koichi, Hayashi, Miki, Hanzawa, Yuji
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.02.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
QUINOLINE
ORGANOLITHIUM REAGENTS
ALKYNES
IMINES
ASYMMETRIC CYCLOPROPANATION
CONJUGATE ADDITION
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Summary:The addition of alkenylzirconocene chloride to 3,4-dihydroisoquinoline in the presence of a stoichiometric amount of acylating agent such as (Boc) 2O or ClCOOC 2H 5 was carried out in the presence of a catalytic amount of Cu(I) (10 mol %) to give an alkenylation–carbamation product. The enantioselective addition (56–75%ee) of the alkenylzirconocene chloride was also achieved under Cu(I)/chiral amine (10 mol %) conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.11.078