Concepedia

Enantioselective Iridium‐Catalyzed Allylation of Acetylenic Ketones via 2‐Propanol‐Mediated Reductive Coupling of Allyl Acetate: C14‐C23 of Pladienolide D

Gilmar A. Brito, Woo‐Ok Jung, Minjin Yoo, Michael J. Krische

Angewandte Chemie International Edition · 2019 · 19 citations · 52 references

DOIFull text

Open access

Concepts

Abstract

Highly enantioselective catalytic reductive coupling of allyl acetate with acetylenic ketones occurs in a chemoselective manner in the presence of aliphatic or aromatic ketones. This method was used to construct C14-C23 of pladienolide D in half the steps previously required.

References

52

Enantioselective Catalytic Formation of Quaternary Stereogenic Centers

Pier Giorgio Cozzi, Robert Hilgraf · European Journal of Organic Chemistry · 2007 · 545 citations

, , +7

Metal‐Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl‐Type Compounds

Toni Moragas, Arkaitz Correa, Rubén Martı́n · Chemistry - A European Journal · 2014 · 525 citations · Full text

, , +10

H3B-8800, an orally available small-molecule splicing modulator, induces lethality in spliceosome-mutant cancers

Michael Seiler, Akihide Yoshimi, Rachel Darman et al. · Nature Medicine · 2018 · 510 citations · Full text

, , +15

Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranes

Herbert C. Brown, K. S. BHAT · Journal of the American Chemical Society · 1986 · 380 citations

, , +5

Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess

Prabhakar K. Jadhav, K. S. BHAT, Paramasivan T. Perumal et al. · The Journal of Organic Chemistry · 1986 · 356 citations

, , +6