The Development of a Sulfamate-Tethered Aza-Michael Cyclization Allows for the Preparation of (−)-Negamycin tert-Butyl Ester

We present the first examples of intramolecular aza-Michael cyclizations of sulfamates and sulfamides onto pendant α,β-unsaturated esters, thioesters, amides, and nitriles. Stirring the substrate with catalytic quantities of the appropriate base delivers the product in good yield and excellent diast...

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Published inJournal of organic chemistry Vol. 89; no. 8; pp. 5911 - 5916
Main Authors Joshi, Harshit, Nirpal, Appasaheb K., Paul, Debobrata, Kelley, Steven P., Mague, Joel T., Sathyamoorthi, Shyam
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ALCOHOLS
DRUG
NUCLEOPHILE
ASYMMETRIC-SYNTHESIS
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Summary:We present the first examples of intramolecular aza-Michael cyclizations of sulfamates and sulfamides onto pendant α,β-unsaturated esters, thioesters, amides, and nitriles. Stirring the substrate with catalytic quantities of the appropriate base delivers the product in good yield and excellent diastereoselectivity. The reactions are operationally simple, can be performed open to air, and are tolerant of a variety of important functional groups. We highlight the utility of this technology by using it in the preparation of a (−)-negamycin derivative.
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Harshit Joshi and Appasaheb K. Nirpal contributed equally.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00604