Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 43, Pages 17983-17988Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c09742
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Funding
- NSFC [22031004, 21921003, 21702063]
- Shanghai Municipal Education Commission [20212308]
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This study presents a Pd-catalyzed enantioselective three-component coupling for the synthesis of chiral diarylmethyl alkynes using a novel chiral ligand. The method features readily available starting materials, high enantioselectivity, and ease of operation.
Significant attention has been given in the past few years to the selective transformations of N-tosylhydrazones to various useful compounds. However, the development of enantioselective versions poses considerable challenges. Herein we report a Pd-catalyzed enantioselective three-component coupling of N-tosylhydrazone, aryl halide, and terminal alkyne under mild conditions utilizing a novel chiral sulfinamide phosphine ligand (GF-Phos), which provides a facile access to chiral diarylmethyl alkynes, which are useful synthons in organic synthesis as well as exist as the skeleton in many bioactive molecules. A pair of enantiomers of the product could be easily prepared using the same chiral ligand by simply changing the aryl substituents of the N-tosylhydrazone and aryl halide. The salient features of this reaction include the readily available starting materials, general substrate scope, high enantioselectivity, ease of scale-up, mild reaction conditions, and versatile transformations.
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