Oxidative Cyclization of Sulfamates Onto Pendant Alkenes

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2020 Jan 14

PMID 31927967

Citations 17

Authors

Anand H Shinde

Shyam Sathyamoorthi

Affiliations

Soon will be listed here.

Abstract

This communication discloses the first examples of aza-Wacker cyclizations of sulfamate esters. Within the realm of related cyclization reactions, this protocol is differential in that it forms six-membered rings in good yield and uses catalytic amounts of palladium(0) rather than palladium(II) salts. These reactions scale well, and their products are demonstrated to be valuable synthetic intermediates.

Citing Articles

A Catalytic, Enantioselective Sulfamate Tethered -Michael Cyclization.

Joshi H, Manna A, Nagamalla S, Thomas A, Sathyamoorthi S Org Lett. 2024; 26(50):10708-10713.

PMID: 39660506 PMC: 11662505. DOI: 10.1021/acs.orglett.4c03558.

Exploration of One-Pot, Tandem Sulfamoylation and -Michael Cyclization Reactions for the Syntheses of Oxathiazinane Dioxide Heterocycles.

Nirpal A, Joshi H, Kelley S, Sathyamoorthi S J Org Chem. 2024; 89(22):16774-16778.

PMID: 39492674 PMC: 11567779. DOI: 10.1021/acs.joc.4c02086.

Taming Tethered Nitreniums for Alkene Functionalization Reactions.

Silver R, Nirpal A, Sathyamoorthi S J Org Chem. 2024; 89(20):15352-15357.

PMID: 39387609 PMC: 11827887. DOI: 10.1021/acs.joc.4c01886.

Fun With Unusual Functional Groups: Sulfamates, Phosphoramidates, and Di-tert-butyl Silanols.

Sathyamoorthi S European J Org Chem. 2024; 27(9).

PMID: 39309710 PMC: 11415259. DOI: 10.1002/ejoc.202301283.

Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework.

Wu J, Tan X, Wu W, Jiang H Nat Commun. 2024; 15(1):6776.

PMID: 39117681 PMC: 11310316. DOI: 10.1038/s41467-024-51173-4.

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