2017
DOI: 10.1021/acs.orglett.7b00051
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Metal-Free Cycloetherification by in Situ Generated P-Stereogenic α-Diazanium Intermediates: A Convergent Synthesis of Enantiomerically Pure Dihydrobenzooxaphospholes

Abstract: A metal-free tandem reaction, initiated by the generation of a diazonium cation and followed by cycloetherification, was developed. Acid-promoted de-tert-butylation of N-nitroso N-tert-butylamine was used to generate a diazonium cation in situ, demonstrating a new application of nitroso chemistry. This reaction was employed in the synthesis of substituted benzofuran-3(2H)-ones and dihydrobenzo[d][1,3]oxaphosphole 3-oxides.

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Cited by 4 publications
(18 citation statements)
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“…The combined organic layers were dried over MgSO 4 and concentrated to give 13 (6.35 g, 96%) as a pale-yellow oil which was used without further purification; 1 . The 1 H and 13 C spectral data were in accordance with those previously reported [14] (Supplementary Materials).…”
Section: Synthesis and Rearrangement Of Ethyl P-(4-benzyloxyphenyl)-n...supporting
confidence: 88%
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“…The combined organic layers were dried over MgSO 4 and concentrated to give 13 (6.35 g, 96%) as a pale-yellow oil which was used without further purification; 1 . The 1 H and 13 C spectral data were in accordance with those previously reported [14] (Supplementary Materials).…”
Section: Synthesis and Rearrangement Of Ethyl P-(4-benzyloxyphenyl)-n...supporting
confidence: 88%
“…The same procedure as in 2.3.1 using 2-bromophenol (6.08 g, 35 mmol), K 2 CO 3 (6.64 g, 48 mmol), and 2-methoxybenzyl bromide (6.64 g, 35 mmol) gave 18d (9.10 g, 81%) as a yellow oil; ν max /cm −1 1510, 1310, 1270, 1080, 1060, and 760; 1 H NMR (300 MHz): 7.60 (1H, m, ArH), 7.55 (1H, dd J = 8.0, 1.2 Hz, ArH), 7.28 (1H, m, ArH), 7.21 (1H, m, ArH), 7.01-6.95 (2H, m, ArH), 6.87 (1H, m, ArH), 6.82 (1H, ddd J = 8.1, 7.8, 1.5 Hz, ArH), 5.19 (2H, s, OCH 2 ) and 3.86 (3H, s, OCH 3 ); 13…”
Section: -Bromophenyl 2-methoxybenzyl Ether 18dmentioning
confidence: 99%
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