Binary 1,4-asymmetric induction toward imines from a single allyltin reagent with a chiral oxygen functional group

A single allyltin reagent possessing a chiral oxygen functional group afforded each diastereomeric product in the reaction with N-sulfonylimines promoted by appropriate Lewis acids in a binary stereoselective manner. InCl 3 selectively provided the syn-1,4-amino alcohol derivatives, while BF 3 and T...

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Bibliographic Details
Published in:Tetrahedron letters 2010-12, Vol.51 (48), p.6298-6300
Main Authors: Nishigaichi, Yutaka, Fujimoto, Takahiro, Takuwa, Akio, Iwamoto, Hidetoshi
Format: Article
Language:English
Subjects:
1,4-Aminoalcohol derivatives
Alcohols
Allyltin
Asymmetric induction
Derivatives
Functional groups
Imines
Lewis acid
Sulfonylimine
Tetrahedrons
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Summary:A single allyltin reagent possessing a chiral oxygen functional group afforded each diastereomeric product in the reaction with N-sulfonylimines promoted by appropriate Lewis acids in a binary stereoselective manner. InCl 3 selectively provided the syn-1,4-amino alcohol derivatives, while BF 3 and TiCl 4 gave the anti-products preferentially.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.09.104