2018
DOI: 10.1021/acs.orglett.8b00867
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Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of N-Sulfonylamidine Derivatives

Abstract: A novel, secondary amide activation strategy has been developed through the in situ generation of ylides from amides and diazoacetates. Under the developed reaction conditions, Mn-catalyzed ylide formation and interception reaction by sulfonamide delivered a variety of N-sulfonylamidines. Notably, when highly active Zn(OTf) was used as the catalyst, further N-H insertion products were obtained. In contrast with traditional methods, our amide activation strategy is distinguished by accessible starting material,… Show more

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Cited by 34 publications
(23 citation statements)
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“…Following the general procedure B with N,N-dioctylamine 18a, the title compound 18b was obtained as a slowly crystallizing colorless oil in 82% yield. Following a previously reported procedure, [1] isopropyl alcohol (5.00 mmol, 1 equiv.) and NaHCO3 (1.26g, 15.0 mmol, 3 equiv.)…”
Section: Ethyl Dioctylglycinate (18b)mentioning
confidence: 99%
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“…Following the general procedure B with N,N-dioctylamine 18a, the title compound 18b was obtained as a slowly crystallizing colorless oil in 82% yield. Following a previously reported procedure, [1] isopropyl alcohol (5.00 mmol, 1 equiv.) and NaHCO3 (1.26g, 15.0 mmol, 3 equiv.)…”
Section: Ethyl Dioctylglycinate (18b)mentioning
confidence: 99%
“…Following a previously reported procedure, [1] cyclohexyl alcohol (5.00 mmol, 1 equiv.) and NaHCO3 (1.26g, 15.0 mmol, 3 equiv.)…”
Section: Synthesis Of Cyclohexyl 2-bromoacetate 20mentioning
confidence: 99%
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