105367-34-8

Upstream product

• 100-42-5 styrene 
• 35059-50-8 t-butyl diazoacetate 
• 2051-95-8 succinylbenzene 
• 55666-45-0 4-oxo-4-phenyl-butyric acid tert-butyl ester 
• 1006728-95-5 (S)-tert-butyl 4-hydroxy-4-phenylbutanoate 
• 100-52-7 benzaldehyde 
• 1663-39-4 tert-Butyl acrylate 
• 1314323-92-6 (1R,2R)-tert-butyl 2-(3-bromophenyl)cyclopropanecarboxylate 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 141362-75-6 Bis-{(S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4,5-dihydro-3H-pyrrol-2-yl}-methyl-amine 
• 141362-74-5 Methyl-bis-[(S)-5-(1-methyl-1-trimethylsilanyloxy-ethyl)-4,5-dihydro-3H-pyrrol-2-yl]-amine 

Relevant academic research and scientific papers

Synthesis of a new chiral nonracemic C2-symmetric 2,2′-bipyridyl ligand and its application in copper(I)-catalyzed enantioselective cyclopropanation reactions

An efficient synthesis of a low molecular weight, chiral nonracemic and (C2-symmetric bipyridyl ligand is reported. The ligand was prepared using a catalytic asymmetric dihydroxylation reaction of a pyrindine as a key step. The ligand was evalu

Asymmetric Carbene C-O Insertion Using Optically Active Bipyridine-Copper Complex as a Catalyst. Ring Expansion of Oxetanes to Tetrahydrofurans

Copper complex of (7R,7R')-di(1-t-butyldimethylsiloxy-1-methylethyl)-6,6',7,7'-tetrahydro-5H,5'H-2,2'-bi-1,1'-pyridine (3) was found to be an effective catalyst for asymmetric carbene insertion reaction into the C-O bond of oxetanes.For example, the react

Catalytic asymmetric cyclopropanation using copper complex of optically active bipyridine as a catalyst

Optically active 8,8'-di(trimethylsilyl)-5,5',6,6',7,7',8,8'-octahydro-2,2'- biquinoline (7) was found to be an effective catalyst for enantioselective cyclopropanation of olefins. For example, the reaction of styrene and t-butyl diazoacetate in the presence of 7 proceeded with high enantioselectivity of 92% ee, to give t-butyl trans-2-phenylcyclopropanecarboxylate. On the other hand, the reaction of trans-β-methylstyrene gave the cis-isomer of >99% ee as a major product.

C2-symmetric fluorous diamines and diimines as ligands for metal-catalysed asymmetric cyclopropanation of styrene

Perfluoroalkyl-substituted, enantiopure C2-symmetric N and N,O ligands showing affinity either for standard organic solvents or perfluorocarbons have been conveniently prepared from readily available precursors. Preformed cobalt(II) and in-situ-generated copper(I) complexes of these ligands were tested as catalysts in the metal-catalysed cyclopropanation of styrene with diazoacetates. Under optimised reaction conditions, which include the use of a fluorous biphasic system and short reaction times, the copper complex of a C2-symmetric diamine afforded promising results (yield = 77%, trans/cis = 67:33, ee of the trans isomer = 62%) and could be easily separated from the products by simply decanting the fluorous phase. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

cis-Selective cyclopropanations using chiral 5,5-diaryl bis(oxazoline) catalysts

A series of 5,5-diaryl bis(oxazolines) have been prepared and used as ligands in the copper catalysed asymmetric cyclopropanation of styrene. Unusually, for bis(oxazolines), the diastereoselectivity of the process favoured the cis cyclopropanes with diastereomeric ratios of up to 65:35 being realised. The cis selectivity of the process was rationalised in terms of repulsion between the alkene substituent and the pro-R 5-aryl group of the bis(oxazoline). (C) 2000 Published by Elsevier Science Ltd.

Cyclopropanation reactions catalysed by ruthenium complexes with new anionic phosphine ligands

Novel ruthenium complexes with anionic phosphine ligands were found to be efficient In the catalytic cyclopropanation reaction of olefins with ethyl diazoacetate.

Chiral ligands with pyridine donors in transition metal catalyzed enantioselective cyclopropanation and hydrosilylation reactions

Copper(I) and rhodium(I) complexes prepared in situ from [Cu(OTf)(C6H6)0.5] and [Rh(cod)Cl]2 with a range of chiral 2,2'-bipyridines, 5,6-dihydro-1,10-phenanthrolines, 1,10-phenanthrolines and 2,2':6',2''-terpyridines were assessed as chiral catalysts for the enantioselective cyclopropanation of styrene with diazoacetates and for the hydrosilylation of acetophenone with diphenylsilane. Enantioselectivities up to 68% in the cyclopropanation and up to 32% in the hydrosilylation were obtained. Copyright (C) 2000 Elsevier Science Ltd.

Highly enantioselective cyclopropanation of styrene derivatives using Co(III)-salen complex as a catalyst

Optically active (salen)cobalt(III) bromide complex 6-Br was found to be an efficient catalyst for asymmetric cyclopropanation of styrene derivatives. For example, the reaction of 4-chlorostyrene and tert-butyl diazoacetate in the presence of 6-Br proceeded with high enantioselectivity of 96% ee as well as high trans-cis selectivity (97:3) to give tert-butyl 2-(4-chlorophenyl)cyclopropane-1-carboxylate as a major product.

A new class of bis-oxazoline ligands for the Cu-catalysed asymmetric cyclopropanation of olefins

A set of new chiral bis-oxazolines, 5a-b and 6a-c, has been synthesised from D and L-diethyl 2,3-O-isopropylidene tartrates and chiral amino alcohols. These ligands were found to be efficient in the Cu(I)-catalysed asymmetric cyclopropanation of olefins.

Construction of an aryliridium-salen complex for highly cis- and enantioselective cyclopropanations

(Chemical Equation Presented) Ringing the changes: Iridium(lll)-salen complexes 1 bearing a σ-coordinated aryl ligand (L = CH3C 6H4, C6H5) at the apical position are found to efficiently catalyze the cis- and enantioselective cyclopropanation of mono- and disubstituted olefins (see scheme).