65488-06-4

Upstream product

• 123485-57-4 (S)-1-{[((S)-4-Chloro-1-phenyl-butyl)-dimethyl-silanyl]-methyl}-2-methoxymethyl-pyrrolidine 
• 33553-82-1 4-chloro-1-phenyl-1-butanol 
• 160550-43-6 Acetic acid 4-chloro-1-phenyl-butyl ester 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 5356-99-0 benzyl chloromethyl dimethyl silane 
• 123463-20-7 [(S)-2-(methoxymethyl)pyrrolidinomethyl]dimethyl benzylsilane 

Downstream Products

• 16133-83-8 (S)-2-phenyltetrahydrofuran 

Relevant academic research and scientific papers

A trans-chelating bisphosphine possessing only planar chirality and its application to catalytic asymmetric reactions

A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45% overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94% ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77% ee.

Hydrazide-Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis-Decalins

Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (E)-polyenes to form trans-decalin ring systems are well precedented, highly enantioselective cyclizations of (Z)-polyenes to form the correspond

Mesoporous silica KIT-6 supported superparamagnetic CuFe2O 4 nanoparticles for catalytic asymmetric hydrosilylation of ketones in air

A diverse range of prochiral ketones were reduced in air with high yields and good-to-excellent enantioselectivities (up to 97% ee) in the presence of a heterogeneous catalyst system, which was in situ formed from catalytic amounts of superparamagnetic CuFe2O4 nanoparticles supported on mesoporous silica KIT-6 and non-racemic dipyridylphosphine ligand, the stoichiometric hydride donor polymethylhydrosiloxane (PMHS) as well as certain amounts of additives. The magnetically separable catalysts could be efficiently reused 4 times without apparent loss of both the activity and enantioselectivity. the Partner Organisations 2014.

Iridium complexes with chiral and achiral β-aminophosphane ligands: Catalysts for >C=O hydrogenation and H/D exchange involving both homo-and heterolytic H2 activation

Chiral and achiral P,N-chelated IrI complexes of the general type [(COD)Ir(P∩NR1R2)]BF4, where COD = η4-1,5-C8H12 and P∩NR1R 2 = (1R,2R)-, (1S,2S)-, or (1R,2S)-Ph2PC 1H(Ph)C2H(Me)NR1R2 (NR 1R2 = NH2, NHMe, NHCH2Ph, NHCHMe2, NMe2), Ph2PCH2CR 2NH2 (R = H, Me), of 2-Ph2PC6H 4NHMe, have been prepared by treating [Ir(COD)2]BF 4 with the required β-aminophosphane in THF. The monolithiated ligands Ph2PCH2CMe2N(Li)H and 2-Ph 2PC6H4N(Li)Me interacted with [{(COD)Ir(μ-Cl))2] to give the neutral alkyl- and arylamido compounds [(COD)-Ir(Ph2PCH2CMe2NH)] and [(COD)Ir(2-Ph2PC6H4NMe)]. All IrI complexes [(COD)Ir(P∩NR1R2)]BF4 acted as catalysts for the direct hydrogenation of alkyl aryl ketones to the corresponding 1-phenylalkanols, if combined with an alkaline or amine base in methanol under H2 (10-50 bar) between 25 and 50 °C. The reaction occurred with modest to moderate enantioselectivity (ca. 20-75% ee) if chelate complexes bearing the various optically active β-aminophosphanes were used as catalysts. The base-free amido complexes [(COD)-Ir(P∩NR)] displayed similar catalytic activity to the combined systems [(COD)Ir(P∩NHR)]BF 4-KOH (P∩NHR = Ph2PCH2CMe 2NH2, 2-Ph2PC6H4NHMe). The ability of both the cationic β-amino- and the neutral β-amidophosphane IrI complexes to undergo oxidative H 2 addition and the observation of H2/D+ as well as H2/D2 exchange processes during catalysis provided evidence for a mechanism involving reversible "[IrIII(H) 2-P∩NHR]+ ? [(η2-H2)-Ir III(H)-P∩NR]+" proton-to-hydride transfer and heterolytic H2 cleavage on amino-dihydride and amido-dihydrogen- monohydride tautomers. The crystal structures of [(COD)Ir{(1S,2S)-Ph 2PCH(Ph)CH(Me)NHCH2Ph}]BF4·2THF, [(COD)Ir{1R,2S-Ph2PCH(Ph)CH(Me)NHMe}]BF4·THF, and the orthometalated 18e IrI complex [(COD)Ir{(1R,2S)-Ph 2PCH(C6H4-o)-CH(Me)NHCHMe2}], which resulted from treatment of [(COD)Ir{(1R,2S)-Ph2PCH(Ph)CH(Me) NHCHMe2}]BF4 with excess KOH, have been determined by single crystal X-ray diffraction studies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Enzymatic preparation of optically active 4-Chloro-1-phenyl-1-butanol derivatives

The enantiomers of substituted 4-chloro-1-phenyl-1-butanol were prepared by stereoselective lipasecatalyzed resolution of the corresponding esters and alcohols, in water and in organic solvent, respectively.