[1,2]‐Phospha‐Brook Rearrangement as Tool for Generation of Anionic Nucleophiles in Addition Reactions under Brønsted Base Catalysis-Reference-Cited by-同舟云学术

[1,2]‐Phospha‐Brook Rearrangement as Tool for Generation of Anionic Nucleophiles in Addition Reactions under Brønsted Base Catalysis

Published:2023-02-07 Issue:3 Volume:12 Page:
ISSN:2193-5807
Container-title:Asian Journal of Organic Chemistry
language:en
Short-container-title:Asian J Org Chem

Author:

Kondoh Azusa¹^ORCID,Terada Masahiro²^ORCID

Affiliation:

1. Research and Analytical Center for Giant Molecules Graduate School of Science Tohoku University Aramaki, Aoba-ku Sendai 980-8578 Japan

2. Department of Chemistry, Graduate School of Science Tohoku University Aramaki, Aoba-ku Sendai 980-8578 Japan

Abstract

AbstractThe [1,2]‐phospha‐Brook rearrangement involves the migration of the dialkoxyphosphoryl moiety of the alkoxide of an α‐hydroxyphosphonate from carbon to oxygen to generate an α‐oxygenated carbanion. The alkoxide that is the precursor for the rearrangement is easily accessible by the deprotonation of α‐hydroxyphosphonates or the addition of the anion of secondary phosphites to carbonyl compounds under the influence of a Brønsted base. This review article summarized recent development of the Brønsted base‐catalyzed addition reactions in which the [1,2]‐phospha‐Brook rearrangement is utilized for the generation of carbon‐based anionic nucleophiles.

Publisher

Wiley

Subject

Organic Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ajoc.202300003

Reference77 articles.

1. For reviews on Brønsted base catalysis see:

2. Superbases for Organic Synthesis 2009

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