4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 48, Pages 6298-6300

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.09.104

Keywords

Allyltin; 1,4-Aminoalcohol derivatives; Asymmetric induction; Lewis acid; Sulfonylimine

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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. (C) 2010 Elsevier Ltd. All rights reserved.

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