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Stereoconvergent Chiral Inductive Diastereodivergent Sulfonamidation of Diastereomixtures of Diarylmethanols with Sulfonylamine Catalyzed by Lewis Acids

Author:
Yamamoto, Hiroshi, Nakata, Kenya
Source:
Organic letters 2018 v.20 no.22 pp. 7057-7061
ISSN:
1523-7052
Subject:
Lewis acids, aromatic compounds, catalysts, ferric chloride, moieties, optical isomerism
Abstract:
Diastereodivergent sulfonamidation of diastereomixtures of diarylmethanols bearing a chiral auxiliary using a sulfonylamine was achieved by use of SnCl₂ and FeCl₃ as the Lewis acid catalysts in nitromethane under mild reaction conditions. Both reaction conditions were applicable to a broad substrate scope, irrespective of the substituents on the aromatic ring of the substrates. The nosyl group and the chiral auxiliary were easily deprotected under the general conditions without any erosion of chirality.
Agid:
6212542