Methodology

BINAP–Ruthenium Catalyzed Asymmetric Hydrogenation: Noyori's Foundational Platform

The combination of (BINAP)RuCl₂ with a chiral 1,2-diamine co-ligand, recognized by the 2001 Nobel Prize awarded to Ryoji Noyori, established the modern field of asymmetric …

2026-06-10

CBS Reduction: Enantioselective Borane Reduction of Prochiral Ketones

The Corey–Bakshi–Shibata (CBS) reduction uses a chiral oxazaborolidine to activate borane (BH₃·THF or BH₃·Me₂S) for the enantioselective reduction of prochiral ketones. Reported in …

2026-06-05

Chiral Phosphoric Acid Catalysis with TRIP-BINOL: Organocatalytic Asymmetric Activation

Chiral phosphoric acids (CPAs) derived from 3,3’-disubstituted BINOL have, since the seminal work of Akiyama and Terada around 2004, grown into one of the most versatile …

2026-05-28

Olefin Metathesis with Grubbs and Hoveyda–Grubbs Second-Generation Catalysts

Olefin metathesis, recognized by the 2005 Nobel Prize awarded to Chauvin, Grubbs, and Schrock, has become a routine C–C bond-forming reaction in medicinal and process chemistry. …

2026-05-22

Buchwald Biaryl Phosphine Ligands: Revolutionizing Palladium-Catalyzed Cross-Coupling

Palladium-catalyzed cross-coupling has been transformed over the past two decades by Stephen Buchwald’s development of electron-rich, sterically demanding biaryl phosphine …

2026-05-15

NHC-Catalyzed Organic Transformations with IMes and IPr Precatalysts

N-heterocyclic carbenes (NHCs) have, since the late 1990s, become indispensable ligands in transition-metal catalysis. The two most widely used NHCs — IMes …

2026-05-08

Spiro Bisphosphine Ligands: SPINOL and SIPHOS in Asymmetric Catalysis

Chiral spiro ligands, developed primarily by Zhou Qi-Lin and coworkers at Nankai University, occupy a distinctive position in the ligand landscape. Their defining feature is a …

2026-04-22

Jacobsen Mn-Salen Catalysts for Asymmetric Epoxidation of Unfunctionalized Olefins

Eric Jacobsen’s Mn(III)-salen complex, introduced in 1990, solved a long-standing problem: the enantioselective epoxidation of unfunctionalized olefins. Unlike the Sharpless …

2026-04-08

MacMillan Imidazolidinone Organocatalysts: SOMO Catalysis and Asymmetric Diels–Alder

David MacMillan’s imidazolidinone organocatalysts, introduced in 2000, established iminium activation as a complementary strategy to enamine catalysis. The catalysts condense …

2026-03-30

Cinchona Alkaloids in Asymmetric Organocatalysis and Phase-Transfer Catalysis

Cinchona alkaloids — cinchonidine, cinchonine, quinine, and quinidine — are among the oldest chiral catalysts in organic chemistry. Extracted from the bark of Cinchona trees, these …

2026-03-22

Jørgensen–Hayashi Diarylprolinol Silyl Ethers in Enamine and Iminium Catalysis

The Jørgensen–Hayashi catalyst — a chiral diphenylprolinol silyl ether — emerged around 2005 as a solution to the long-standing problem of enantioselective α-functionalization of …

2026-03-15

BINAL-H: Noyori's Chiral Hydride Reagent for Enantioselective Reduction

BINAL-H, introduced by Noyori in 1979, is a chiral modifying reagent formed by combining lithium aluminum hydride (LiAlH₄) with equimolar (S)- or (R)-BINOL and ethanol. The …

2026-03-08

BOX Ligands in Lewis Acid Catalysis: t-Bu-BOX and Asymmetric Cycloadditions

Bisoxazoline (BOX) ligands, developed in the 1990s by Pfaltz, Ghosh, and Evans, are the dominant chiral scaffolds for Lewis acid-catalyzed asymmetric reactions. The …

2026-02-28

TADDOL and DIOP Ligands in Asymmetric Titanium and Rhodium Catalysis

TADDOL (α,α,α’,α’-tetraaryl-1,3-dioxolane-4,5-dimethanol) and DIOP (2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane) are two foundational chiral …

2026-02-20

Methodology, Science 8 tags

Privileged Chiral Bisphosphine Ligands: From DIPAMP to BINAPINE

Chiral bisphosphine ligands are the cornerstone of asymmetric hydrogenation. The evolution from DIPAMP (1970s) through CHIRAPHOS, PROPHOS, and SEGPHOS to modern variants like …

2026-02-12

Phosphoramidite Ligands: MonoPhos and the Modular Approach to Asymmetric Catalysis

Phosphoramidite ligands, introduced by Feringa and de Vries in the late 1990s, are a modular class of monodentate chiral phosphorus ligands derived from BINOL and secondary amines. …

2026-02-05