Concepedia

Synthesis of α-keto esters by the rhodium-catalysed reaction of cyanoformate with arylboronic acids

Hiroshi Shimizu, Masahiro Murakami

Chemical Communications · 2007 · 74 citations · 46 references

DOI

Concepts

Abstract

An arylrhodium(I) species selectively reacts with the cyano group of ethyl cyanoformate to afford the corresponding alpha-keto ester in good yield.

References

46

Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium Intermediates

Tamio Hayashi, Makoto Takahashi, Yoshiaki Takaya et al. · Journal of the American Chemical Society · 2002 · 585 citations

, , +15

<i>C</i><sub>2</sub>-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands:  Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of <i>N</i>-Tosylarylimines

Norihito Tokunaga, Yusuke Otomaru, Kazuhiro Okamoto et al. · Journal of the American Chemical Society · 2004 · 426 citations

, , +13

Rhodium-Catalyzed Hydroarylation of Alkynes with Arylboronic Acids:  1,4-Shift of Rhodium from 2-Aryl-1-alkenylrhodium to 2-Alkenylarylrhodium Intermediate

Tamio Hayashi, Kazuya Inoué, Nobukazu Taniguchi et al. · Journal of the American Chemical Society · 2001 · 347 citations

, , +4

Rhodium‐Catalyzed Asymmetric Addition of Aryl‐ and Alkenylboronic Acids to Isatins

Ryo Shintani, Mitsunori Inoue, Tamio Hayashi · Angewandte Chemie International Edition · 2006 · 321 citations

, , +8

Regioselective synthesis of β-ketoesters from lithium enolates and methyl cyanoformate

Lewis N. Mander, S. P. SETHI · Tetrahedron Letters · 1983 · 319 citations

, , +6