Construction\nof 4‑Vinyl-1,2-oxaphospholane\n2‑Oxides from Vinyloxiranes and Phosphoryl Diazomethanes

Various 4-vinyl-1,2-oxaphospholane 2-oxides are prepared\nin good\nto excellent yields from vinyloxiranes and in situ-generated phosphenes\nfrom phosphoryl diazomethanes via the phosphene-induced ring expansion\nof oxiranes. The reaction is a novel and expeditious strategy for\nthe synthesis of 1,2-oxaphospholane 2-oxide derivatives, featuring\nring expansion of readily available starting materials, high atom\neconomy, no catalyst, a fast reaction rate, broad functional group\ntolerance, high yields, and separable diastereomers.

Publication Details

Journal
Figshare
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c04105.s001
Primary Topic
Organophosphorus compounds synthesis
Type
article
Field-Weighted Citation Impact
0.00
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article

Construction\nof 4‑Vinyl-1,2-oxaphospholane\n2‑Oxides from Vinyloxiranes and Phosphoryl Diazomethanes

Figshare
Organophosphorus compounds synthesis
article

Construction\nof 4‑Vinyl-1,2-oxaphospholane\n2‑Oxides from Vinyloxiranes and Phosphoryl Diazomethanes

article en

Abstract

Various 4-vinyl-1,2-oxaphospholane 2-oxides are prepared\nin good\nto excellent yields from vinyloxiranes and in situ-generated phosphenes\nfrom phosphoryl diazomethanes via the phosphene-induced ring expansion\nof oxiranes. The reaction is a novel and expeditious strategy for\nthe synthesis of 1,2-oxaphospholane 2-oxide derivatives, featuring\nring expansion of readily available starting materials, high atom\neconomy, no catalyst, a fast reaction rate, broad functional group\ntolerance, high yields, and separable diastereomers.

Figshare
Openalex Percentile: Top 76%
Organophosphorus compounds synthesis
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Construction\nof 4‑Vinyl-1,2-oxaphospholane\n2‑Oxides from Vinyloxiranes and Phosphoryl Diazomethanes · Figshare (2024) | TGRS Research Map | TGRS