Dinuclear zinc catalyzed asymmetric Friedel-Crafts amidoalkylation of indoles with aryl aldimines.

The asymmetric Friedel-Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85-98%) with moderate to high enantiomeric ratios (from 70 : 30 up to 95 : 5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl methanamines, which avoids the formation of the undesirable bis- and tris(indolyl)methanes (BIMs and TIMs) byproduct.

[1]  T. Akiyama,et al.  Chiral Brønsted acid catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2- and 3-substituted indole derivatives. , 2010, Organic & biomolecular chemistry.

[2]  T. Tsubogo,et al.  Highly enantioselective Friedel-Crafts-type alkylation reactions of indoles with chalcone derivatives using a chiral barium catalyst. , 2010, Chemistry, an Asian journal.

[3]  M. Zolfigol,et al.  Bis- and trisindolylmethanes (BIMs and TIMs). , 2010, Chemical reviews.

[4]  Y. Wang,et al.  Catalytic asymmetric hydrophosphinylation of alpha,beta-unsaturated N-acylpyrroles: application of dialkyl phosphine oxides in enantioselective synthesis of chiral phosphine oxides or phosphines. , 2010, Organic letters.

[5]  Lili Lin,et al.  Highly enantioselective synthesis of beta-heteroaryl-substituted dihydrochalcones through Friedel-Crafts alkylation of indoles and pyrrole. , 2010, Chemistry.

[6]  M. Bandini,et al.  Catalytic functionalization of indoles in a new dimension. , 2009, Angewandte Chemie.

[7]  T. Akiyama,et al.  Chiral phosphoric acid catalyzed desymmetrization of meso-1,3-diones: asymmetric synthesis of chiral cyclohexenones. , 2009, Angewandte Chemie.

[8]  M. Bandini,et al.  Enantioselective gold-catalyzed allylic alkylation of indoles with alcohols: an efficient route to functionalized tetrahydrocarbazoles. , 2009, Angewandte Chemie.

[9]  Y. Wang,et al.  Highly enantioselective conjugate additions of phosphites to alpha,beta-unsaturated N-acylpyrroles and imines: a practical approach to enantiomerically enriched amino phosphonates. , 2009, Chemistry.

[10]  S. You,et al.  Asymmetric construction of polycyclic indoles through olefin cross-metathesis/intramolecular Friedel-Crafts alkylation under sequential catalysis. , 2009, Angewandte Chemie.

[11]  M. Zeng,et al.  Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reactions. , 2009, Chemical Society reviews.

[12]  C. Da,et al.  Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst. , 2008, The Journal of organic chemistry.

[13]  B. Trost,et al.  Asymmetric Friedel-Crafts alkylation of pyrroles with nitroalkenes using a dinuclear zinc catalyst. , 2008, Journal of the American Chemical Society.

[14]  M. Terada,et al.  Chiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Reaction of Indoles , 2007 .

[15]  J. Perman,et al.  The highly enantioselective addition of indoles to N-acyl imines with use of a chiral phosphoric acid catalyst. , 2007, Organic letters.

[16]  Q. Kang,et al.  Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid. , 2007, Journal of the American Chemical Society.

[17]  Jun Song,et al.  Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst. , 2006, Journal of the American Chemical Society.

[18]  Qi‐Lin Zhou,et al.  Asymmetric Friedel-Crafts addition of indoles to N-sulfonyl aldimines: a simple approach to optically active 3-indolyl-methanamine derivatives. , 2006, Organic letters.

[19]  J. Esquivias,et al.  A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines: synthesis of unsymmetrical diaryl amines and triaryl methanes. , 2006, Angewandte Chemie.

[20]  B. Trost,et al.  Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes. , 2006, Journal of the American Chemical Society.

[21]  K. Ding,et al.  Intramolecularly Dinuclear Magnesium Complex Catalyzed Copolymerization of Cyclohexene Oxide with CO2 under Ambient CO2 Pressure: Kinetics and Mechanism , 2006 .

[22]  Zheng Wang,et al.  Copolymerization of cyclohexene oxide with CO2 by using intramolecular dinuclear zinc catalysts. , 2005, Chemistry.

[23]  M. Terada,et al.  Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan. , 2004, Journal of the American Chemical Society.

[24]  B. Trost,et al.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction. , 2004, Journal of the American Chemical Society.

[25]  Jian Zhou,et al.  Enantioselective Friedel-Crafts reaction of indoles with arylidene malonates catalyzed by iPr-bisoxazoline-Cu(OTf)2. , 2004, Chemical communications.

[26]  M. Bandini,et al.  New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction. , 2004, Angewandte Chemie.

[27]  Yu Yuan,et al.  Highly enantioselective Friedel-Crafts reaction of aromatic amines with ethyl glyoxylate catalyzed by chiral titanium(IV) complexes: practical synthesis of aminomandelic acid derivatives. , 2004, The Journal of organic chemistry.

[28]  M. Shibasaki,et al.  Catalytic asymmetric Michael reaction of beta-keto esters: effects of the linker heteroatom in linked-BINOL. , 2003, Journal of the American Chemical Society.

[29]  K. Jørgensen,et al.  Asymmetric Friedel-Crafts Reactions: Catalytic Enantioselective Addition of Aromatic and Heteroaromatic C-H Bonds to Activated Alkenes, Carbonyl Compounds, and Imines , 2003 .

[30]  B. Trost,et al.  A direct catalytic asymmetric mannich-type reaction to syn-amino alcohols. , 2003, Journal of the American Chemical Society.

[31]  D. MacMillan,et al.  Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis. , 2002, Journal of the American Chemical Society.

[32]  S. Matsunaga,et al.  Direct catalytic asymmetric aldol reaction: synthesis of either syn- or anti-alpha,beta-dihydroxy ketones. , 2001, Journal of the American Chemical Society.

[33]  S. Saaby,et al.  Formation of Optically Active Aromaticα-Amino Acids by Catalytic Enantioselective Addition of Imines to Aromatic Compounds , 2000 .

[34]  Hisanaka Ito,et al.  A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst Design , 2000 .

[35]  M. Johannsen An enantioselective synthesis of heteroaromatic N-tosyl α-amino acids , 1999 .

[36]  J. Bosch,et al.  PREPARATION OF ENANTIOPURE 6-(3-INDOLYL)-2-PIPERIDONES AND CONJUGATE ADDITIONS TO A 3,4-DIDEHYDRO DERIVATIVE , 1997 .

[37]  Scott R. Wilson,et al.  Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (salen)Manganese Complexes , 1990 .

[38]  T. Katsuki,et al.  Catalytic asymmetric epoxidation of unfunctionalized olefins , 1990 .