Synthesis of 2-phenyl indoxyls

Synthesis of 2-phenyl indoxyls 

ARKIVOC 2006 (xi) 37-46 pp. 37 - 46 

Synthesis of 2-phenylindoxyls
Michael C. Hewitt* and Liming Shao
Drug Discovery, Sepracor Inc., 84 Waterford Drive, Marlborough MA 01752, USA
E-mail: michael.hewitt@sepracor.com
http://www.arkat-usa.org/get-file/23564/


Michael hewitt






10 a  n=1
10a: HPLC Rt = 9.87 min,

1 H NMR (400 MHz, CDCl3)
7.66-7.60 (m, 4H),
7.41-7.37 (m, 3H),
7.11-7.05 (m, 2H),
4.10-4.04 (m, 2H), NCH2
3.69-3.63 (m, 1H), 1H OF OCH2
3.58-3.51 (m, 1H); 1H OF OCH2


13C NMR (100 MHz, CDCl3) 197.2,C=0,  163.9, 137.8, 136.0, 128.9, 128.4, 126.5, 125.7, 122.8, 122.6, 114.8, 99.6, 67.9, 50.1;

http://www.nmrdb.org/13c/index.shtml?v=v2.14.1  PREDICT 13 C NMR

http://www.nmrdb.org/cosy/index.shtml?v=v2.14.1 COSY

GC-MS 13.4 min, M+ 251.

Selected gHMBC couplings (see above): 200 → 7.62, 7.64; 164 → 3.65, 3.5, 7.64; 99 → 3.65, 4.05.



1H NMR PREDICTION BELOW

Michael hewitt

• www.linkedin.com/pub/michael-hewitt/4/580/bb8/en

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New Sc Heterogeneous Catalysts

 

 

New Sc Heterogeneous Catalysts

Three new solid materials are active heterogeneous catalysts for high-yield cyanosilylation of aromatic aldehydes in acetonitrile
Read more

http://www.chemistryviews.org/details/ezine/6451191/New_Sc_Heterogeneous_Catalysts.html

Synthesis of Prostaglandin Analogues, Latanoprost and Bimatoprost, Using Organocatalysis via a Key Bicyclic Enal Intermediate

Synthesis of Prostaglandin Analogues, Latanoprost and Bimatoprost, Using Organocatalysis via a Key Bicyclic Enal Intermediate

Sébastien Prévost , Karen Thai , Nina Schützenmeister , Graeme Coulthard , William Erb , and Varinder K. Aggarwal *

School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, U.K.

Org. Lett., Article ASAP

DOI: 10.1021/ol503520f

Publication Date (Web): January 12, 2015

Copyright © 2015 American Chemical Society

*E-mail: v.aggarwal@bristol.ac.uk.

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

Professor Varinder Aggarwal 
BA, PhD(Cantab), FRS

Professor

Area of research

Asymmetric synthesis, methodology and applications.

Office N226
Cantock's Close,Clifton, Bristol BS8 1TS(See a map)

Tel. +44 (0) 117 954 6315
v.aggarwal@bristol.ac.uk

http://www.chm.bris.ac.uk/org/aggarwal/

School of Chemistry

HIGHLIGHTS

2014
• Nature: Assembly-line synthesis
• Nature Chemistry: Traceless coupling
• Nature Chemistry: sp2-sp3 Coupling
2012
• RSC Symposium: Sven Fritz wins Best Oral presentation
• Nature: Synthesis of prostaglandin PGF2a
• FRS: Varinder elected a Fellow of the Royal Society!
• University College of Dublin: Cath Fletcher wins Best Poster Prize. 
2010
• RSC Symposium: Muhammad Arshad wins Best Prize Prize
• Varinder appears on TV!
2009
• Mike Shaw is awarded Fulbright Distinguished Scholar Fellowship.
2008
• Nature: Enantioselective Conversion of Secondary Alcohols into Tertiary Alcohols

Asymmetric synthesis, methodology and applications.

My research interests include; the development of new catalytic processes for asymmetric synthesis; the development of chiral carbenoids and their use and subsequent applications in catalysis and synthesis; the development of new methodology and its applications in synthesis; total synthesis of biologically important targets.

Research keywords

• catalytic processes
• asymmetric synthesis
• reactive intermediates
• synthesis
• carbenes
• carbenoids

Latest publications

• Bonet, A, Odachowski, M, Leonori, D, Essafi, S & Aggarwal, VK 2014, ‘Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters’. NATURE CHEMISTRY, vol 6., pp. 584-589
• Hesse, MJ, Essafi, S, Watson, CG, Harvey, JN, Hirst, D, Willis, CL & Aggarwal, VK 2014, ‘Highly Selective Allylborations of Aldehydes Using alpha,alpha-Disubstituted Allylic Pinacol Boronic Esters’. Angewandte Chemie International Edition, vol 53., pp. 6145-6149
• Blair, DJ, Fletcher, CJ, Wheelhouse, KMP & Aggarwal, VK 2014, ‘Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (-)-Filiformin’. Angewandte Chemie International Edition, vol 53., pp. 5552-5555
• Pulis, AP, Fackler, P & Aggarwal, VK 2014, ‘Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions’. Angewandte Chemie International Edition, vol 53., pp. 4382-4385
• Mohiti, M, Rampalakos, K, Feeney, KMJ, Leonori, D & Aggarwal, VK 2014, ‘Asymmetric addition of chiral boron-ate complexes to cyclic iminium ions’. Chemical Science, vol 5., pp. 602-607
• Roesner, S, Brown, CA, Mohiti, M, Pulis, AP, Rasappan, R, Blair, DJ, Essafi, S, Leonori, D & Aggarwal, VK 2014,‘Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane’. Chemical Engineering Communications, vol 50., pp. 4053-4055

Cantock's Close

BRISTOL

Efficient Metathesis of Terminal Alkynes

http://onlinelibrary.wiley.com/doi/10.1002/anie.v51.52/issuetoc



Efficient Metathesis of Terminal Alkynes (pages 13019–13022)

Dipl.-Chem. Birte Haberlag, Dr. Matthias Freytag, Dr. Constantin G. Daniliuc, Prof. Dr. Peter G. Jones and Prof. Dr. Matthias Tamm

Article first published online: 14 NOV 2012 | DOI: 10.1002/anie.201207772

Now even terminal: The 2,4,6-trimethylbenzylidyne complexes [MesCM{OC(CF₃)₂Me}₃] (M=Mo, W) were synthesized from [Mo(CO)₆] and [W(CO)₆], respectively. The molybdenum complex is an efficient catalyst for the metathesis of internal and terminal alkynes and also for the ring-closing metathesis of internal and terminal α,ω-diynes at room temperature and low catalyst concentrations.

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"Cyclizative Atmospheric CO2 Fixation by Unsaturated Amines with t-BuOI Leading to Cyclic Carbamates"

"Cyclizative Atmospheric CO₂ Fixation by Unsaturated Amines with t-BuOI Leading to Cyclic Carbamates"
Youhei Takeda, Sota Okumura, Saori Tone, Itsuro Sasaki, and Satoshi Minakata*
Org. Lett. 2012, 14, 4874–4877. DOI: 10.1021/ol302201q 

* Highlighted in "Noteworthy Chemistry" (ACS, October 1, 2012)! （see the detail）
Abstract: A cyclizative atmospheric CO₂ fixation by unsaturated amines such as allyl and propargyl amines under mild reaction conditions, efficiently leading to cyclic carbamates bearing a iodomethyl group, have been developed utilizing tert-butyl hypoiodite (t-BuOI).