Rhodium-Catalyzed Highly Enantioselective Arylation of Cyclic Diketimines: Efficient Synthesis of Chiral Tetrasubstituted 1,2,5-Thiadiazoline 1,1-Dioxides

A highly enantioselective rhodium-catalyzed arylation of cyclic diketimines with arylboronic acids was achieved under mild conditions by employing a simple, sulfinamide-based branched olefin ligand. This protocol provides an efficient access to valuable chiral tetrasubstituted 1,2,5-thiadiazoline 1,...

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Published in:Organic letters 2014-08, Vol.16 (15), p.3962-3965
Main Authors: Wang, Hui, Li, Yi, Xu, Ming-Hua
Format: Article
Language:English
Subjects:
Boronic Acids - chemistry
Catalysis
Imines - chemistry
Molecular Structure
Nitriles - chemistry
Oxides - chemical synthesis
Oxides - chemistry
Rhodium - chemistry
Stereoisomerism
Thiadiazoles - chemical synthesis
Thiadiazoles - chemistry
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cited_by cdi_FETCH-LOGICAL-a381t-738345771fd2a0b1654995e9a809fb6f589cecb95b32d7c6bf18c2b4e59c3eab3
cites cdi_FETCH-LOGICAL-a381t-738345771fd2a0b1654995e9a809fb6f589cecb95b32d7c6bf18c2b4e59c3eab3
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container_title Organic letters
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creator Wang, Hui
Li, Yi
Xu, Ming-Hua
description A highly enantioselective rhodium-catalyzed arylation of cyclic diketimines with arylboronic acids was achieved under mild conditions by employing a simple, sulfinamide-based branched olefin ligand. This protocol provides an efficient access to valuable chiral tetrasubstituted 1,2,5-thiadiazoline 1,1-dioxides in high yields with excellent enantioselectivities of up to 99% ee.
doi_str_mv 10.1021/ol501770q
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subjects Boronic Acids - chemistry
Catalysis
Imines - chemistry
Molecular Structure
Nitriles - chemistry
Oxides - chemical synthesis
Oxides - chemistry
Rhodium - chemistry
Stereoisomerism
Thiadiazoles - chemical synthesis
Thiadiazoles - chemistry
title Rhodium-Catalyzed Highly Enantioselective Arylation of Cyclic Diketimines: Efficient Synthesis of Chiral Tetrasubstituted 1,2,5-Thiadiazoline 1,1-Dioxides
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