Novel synthesis of chiral terminal allenes via palladium(0)-catalyzed reduction of mesylates of 2-bromoalk-2-en-1-ols bearing a protected amino group, using diethylzinc

A novel palladium(0)-catalyzed synthetic route to a series of chiral terminal allenes bearing an N-protected amino alkyl group has been developed. The palladium(0)-catalyzed reaction of mesylates of 2-bromoalk-2-en-1-ols bearing an amino functionality, with diethylzinc affords the corresponding term...

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Bibliographic Details
Published in:Tetrahedron letters 2000-06, Vol.41 (26), p.5131-5134
Main Authors: Ohno, Hiroaki, Toda, Ayako, Oishi, Shinya, Tanaka, Tetsuaki, Takemoto, Yoshiji, Fujii, Nobutaka, Ibuka, Toshiro
Format: Article
Language:English
Subjects:
allenes
diethylzinc
palladium catalysis
reduction
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Summary:A novel palladium(0)-catalyzed synthetic route to a series of chiral terminal allenes bearing an N-protected amino alkyl group has been developed. The palladium(0)-catalyzed reaction of mesylates of 2-bromoalk-2-en-1-ols bearing an amino functionality, with diethylzinc affords the corresponding terminal allenes in good yields. Both ( E)- and ( Z)-bromomesylates can equally be used for the present reaction, yielding the desired allenes in comparable yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00790-5