74497-20-4

Upstream product

• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 124-63-0 methanesulfonyl chloride 
• 17199-29-0 (S)-Mandelic acid 

Downstream Products

• 158800-60-3 dimethyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate 
• 3583-85-5 (-)-(R)-1,2-bis(diphenylphosphino)phenylethane P,P'-dioxide 
• 69381-91-5 (-)-(R)-1,2-bis(diphenylphosphino)-1-phenylethane 

Relevant academic research and scientific papers

One-Pot Synthesis of Cycloocta[b]indole Through Formal [5+3] Cycloaddition Using Donor–Acceptor Cyclopropanes

A new approach to cycloocta[b]indole through formal [5+3] cycloaddition was developed. This methodology was realized by using an indole derivative as a C5 unit and a cyclopropane derivative as a C3 unit. These two units have both donor and acceptor proper

(3+3)-Annulation of Carbonyl Ylides with Donor–Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis

The first (3+3)-annulation process of donor–acceptor cyclopropanes using synergistic catalysis is reported. The Rh2(OAc)4-catalyzed decomposition of diazo carbonyl compounds generated carbonyl ylides in situ. These 1,3-dipoles were c

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.

Accessing substituted pyrrolidines via formal [3+2] cycloaddition of 1,3,5-triazinanes and donor-acceptor cyclopropanes

The formal [3+2] cycloaddition of 1,3,5-triaryl-1,3,5-triazinanes with donor-acceptor cyclopropanes has been found to provide pyrrolidines in good to excellent yields under mild reaction conditions. Preliminary mechanistic investigation indicates that thi

Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles

We herein report a transition-metal-free cross-coupling between secondary alkyl halides/mesylates and aryl/alkenylboronic acid, providing expedited access to a series of nonchiral/chiral coupling products in moderate to good yields. Stereospecific SN2-type coupling is developed for the first time with alkenylboronic acids as pure nucleophiles, offering an attractive alternative to the stereospecific transition-metal-catalyzed C(sp2)-C(sp3) cross-coupling.

Hydrogenation of aromatic-substituted olefins using organoruthenium catalyst

A process is disclosed for the enantioselective hydrogenation of olefins of the formula: STR1 where R is hydrogen or C1 to C6 linear or branched alkyl, Z is STR2 where R' is hydrogen or C1 to C6 linear or branch

The Mechanism of Asymmetric Hydrogenation. Chiral Bis(diphenylphosphino)-α-phenylalkane Complexes in Catalytic and Structural Studies

(R)-1,2-Bis(diphenylphosphino)phenylethane has been synthesised in good overall yield from (S)-mandelic acid ; its cationic rhodium(I) solvated complex has been shown to be effective in catalytic asymmetric hydrogenation with optical yields of up to 88percent having been observed.The n.m.r. spectra of complexes of this phosphine are discussed.Racemic (R*,R*)-1,3-bis(diphenylphosphino)-1,3-diphenylpropane and (R*,R*)-1,4-bis(diphenylphosphino)-1,4-diphenylbutane have been prepared.These form a range of rhodium complexes with dehydroamino-acids whose structures may be assigned on the basis of characteristic n.m.r.P-Rh and P-P coupling constants.

THE MECHANISM OF ASYMMETRIC HOMOGENEOUS HYDROGENATION. SOLVENT COMPLEXES AND DIHYDRIDES FROM RHODIUM DIPHOSPHINE PRECURSORS

Bicyclohepta-2,5-diene and cycloocta-1,5 diene(biphosphine)rhodium tetrafluoroborates react with hydrogen at 1 atmosphere in methanol or other polar solvents.The initial product may be either a solvated dihydride or a solvate; depending on phosphine structure the equilibrium between these two species varies widely.Dihydrides are normally the stable product when the ligand is a monophosphine although (o-methoxyphenyl)methylphenylphosphine is an exception. cis-Chelating biphosphines normally form solvate complexes with no affinity for hydrogen.R-Phenyl bis-diphenylphosphinoethane falls into this category, but the 31P NMR spectra of its complexes demonstrate an equilibrium between monomeric and dimeric species, and addition of triethylamine gives rise to a trimer. trans-Chelating biphosphines show more variable behaviour, and in the case of bis-1,5-diphenylphosphinopentane, a number of complexes, including one requiring C-H activation, are observed.