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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 10
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Original Articles

Enantioselective Deprotonation of Cyclohexene Oxide to (R)-2-Cyclohexen-1-ol

Debnath Bhuniya Department of Chemistry, Indian Institute of Technology, Kanpur, India, 208 016
&
Vinod K. Singh Department of Chemistry, Indian Institute of Technology, Kanpur, India, 208 016
Pages 1475-1481 | Received 04 Nov 1993, Published online: 23 Sep 2006

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Sushil Raina, KamalK. Srivastava, E. Sampath Kumar & VinodK. Singh. (1996) Facile Bromination of O-Benzylidene Sugar and THP Ethers with NBS in Chloroform in the Presence of AIBN. Synthetic Communications 26:1, pages 121-125.
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Articles from other publishers (34)

Nigel S. Simpkins & Michael D. Weller. 2004. Organic Reactions. Organic Reactions 317 636 .
Zvi RappoportFabrice Chemla & Emmanuel Vrancken. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Jingsong You, Andrzej E. Wróblewski & John G. Verkade. (2004) P[(S,S,S)-CH3NCH(CH2Ph)CH2]3N: a new C3-symmetric enantiomerically pure proazaphosphatrane. Tetrahedron 60:36, pages 7877-7883.
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Fabrice Chemla & Emmanuel Vrancken. 2004. The chemistry of organolithium compounds. The chemistry of organolithium compounds 1165 1242 .
Sten O. Nilsson Lill, Peter Dinér, Daniel Pettersen, Mohamed Amedjkouh & Per Ahlberg. 2004. A Tribute Volume in Honor of Professor Osvaldo Goscinski. A Tribute Volume in Honor of Professor Osvaldo Goscinski 1 22 .
. (2003) An Easy and Convenient Synthesis of Optically Active β-Amino Alcohols and 1,2-Diamines. Applications in Enantioselective Deprotonation of Cyclohexene Oxide. Bulletin of the Korean Chemical Society 24:11, pages 1695-1698.
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Goran Angelovski & Peter Eilbracht. (2003) Synthesis of hydroquinone-, biphenol-, and binaphthol-containing aza macroheterocycles via regioselective hydroformylation and reductive amination. Tetrahedron 59:41, pages 8265-8274.
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P Saravanan, Alakesh Bisai, S Baktharaman, M Chandrasekhar & Vinod K Singh. (2002) Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes. Tetrahedron 58:23, pages 4693-4706.
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Sophie K Bertilsson & Pher G Andersson. (2002) Asymmetric base-promoted epoxide rearrangement: achiral lithium amides revisited. Tetrahedron 58:23, pages 4665-4668.
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Sophie K. Bertilsson, Mikael J. Södergren & Pher G. Andersson. (2002) New Catalysts for the Base-Promoted Isomerization of Epoxides to Allylic Alcohols. Broadened Scope and Near-Perfect Asymmetric Induction. The Journal of Organic Chemistry 67:5, pages 1567-1573.
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Roine I. Olsson & Per Ahlberg. (1999) Composition of the activated complex in the stereoselective deprotonation of cyclohexene oxide by a chiral lithium amide. Tetrahedron: Asymmetry 10:20, pages 3991-3998.
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Paul Müller & Patrice Nury. (1999) Copper-Catalyzed Desymmetrization of N -Sulfonylaziridines with Methylmagnesium Halides . Organic Letters 1:3, pages 439-442.
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Sten O. Nilsson Lill, Per I. Arvidsson & Per Ahlberg. (1999) Computational study of solvation and stereoselectivity in deprotonation of cyclohexene oxide by a chiral lithium amide. Tetrahedron: Asymmetry 10:2, pages 265-279.
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Denis Lucet, Thierry Le Gall & Charles Mioskowski. (1998) Die Chemie vicinaler Diamine. Angewandte Chemie 110:19, pages 2724-2772.
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Govindasamy Sekar, Arpita DattaGupta & Vinod K. Singh. (1998) Asymmetric Kharasch Reaction:  Catalytic Enantioselective Allylic Oxidation of Olefins Using Chiral Pyridine Bis(diphenyloxazoline)−Copper Complexes and tert -Butyl Perbenzoate , . The Journal of Organic Chemistry 63:9, pages 2961-2967.
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Peter O’Brien. (1998) Recent advances in asymmetric synthesis using chiral lithium amide bases. Journal of the Chemical Society, Perkin Transactions 1:8, pages 1439.
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Paul G. Williard & Chengzao Sun. (1997) Mixed Aggregates Containing n -Butyl-, sec -Butyl-, or tert -Butyllithium and a Chiral Lithium Amide Derived from N -Isopropyl- O -methyl Valinol . Journal of the American Chemical Society 119:48, pages 11693-11694.
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Aline Corruble, Jean-Yves Valnot, Jacques Maddaluno, Yann Prigent, Daniel Davoust & Pierre Duhamel. (1997) Probing the Origins of Asymmetric Induction by 3-Aminopyrrolidine Lithium Amides Complexes:  A 6 Li/ 1 H/ 13 C NMR Study . Journal of the American Chemical Society 119:42, pages 10042-10048.
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Kazumasa Aoki, Kiyoshi Tomioka, Hiroshi Noguchi & Kenji Koga. (1997) Stereoselective reactions. 28. Effects of the alkyl group at the amide nitrogen of chiral bidentate lithium amides on enantioselective deprotonation reaction. Tetrahedron 53:40, pages 13641-13656.
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Simon E de Sousa, Peter O'Brien & Pierre Poumellec. (1997) Two useful methods for the preparation of (R)- and (S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)ethanamine. Tetrahedron: Asymmetry 8:15, pages 2613-2618.
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Göran Hilmersson, Per I. Arvidsson, Öjvind Davidsson & Mikael Håkansson. (1997) Chiral Lithium Amide/Solute Complexes:  X-ray Crystallographic and NMR Spectroscopic Studies. Organometallics 16:15, pages 3352-3362.
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P. Saravanan, Sushil Raina, T. Sambamurthy & Vinod K. Singh. (1997) A Practical Synthesis of (2 R ,5 R )-2,5-Hexanediol . The Journal of Organic Chemistry 62:8, pages 2669-2670.
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Jason P Tierney, Alexandre Alexakis & Pierre Mangeney. (1997) Catalytic enantioselective deprotonation of meso-epoxides utilising homochiral bis-lithium amide bases. Tetrahedron: Asymmetry 8:7, pages 1019-1022.
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Parthasarathy Saravanan, Arpita DattaGupta, Debnath Bhuniya & Vinod K. Singh. (1997) Studies in the rearrangement of epoxides with lithium dialkylamide-lithium tert-butoxide. Tetrahedron 53:5, pages 1855-1860.
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David M. Hodgson, Andrew R. Gibbs & Gary P. Lee. (1996) Enantioselective desymmetrisation of achiral epoxides. Tetrahedron 52:46, pages 14361-14384.
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Peter O'Brien & Pierre Poumellec. (1996) Chiral base-mediated rearrangement of meso-cyclohexene oxides to allylic alcohols. Tetrahedron Letters 37:44, pages 8057-8058.
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Peter O'Brien & Pierre Poumellec. (1996) A simple and efficient method for the preparation of homochiral amines: Application to the synthesis of a new C2 symmetric triamine. Tetrahedron Letters 37:31, pages 5619-5622.
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Arpita DattaGupta & Vinod K Singh. (1996) Catalytic enantioselective allylic oxidation of olefins with copper complexes of chiral nonracemic bis(oxazolinyl)pyridine type ligands. Tetrahedron Letters 37:15, pages 2633-2636.
Crossref
Agha Zul-Qarnian Khan, Per I. Arvidsson & Per Ahlberg. (1996) Solvent induced isomerization of 2-cyclohexen-1-ol to 3-cyclohexen-1-ol by a chiral lithium amide. Tetrahedron: Asymmetry 7:2, pages 399-402.
Crossref
Debnath Bhuniya, Arpita DattaGupta & Vinod K. Singh. (1996) Design, Synthesis, and Application of Chiral Nonracemic Lithium Amide Bases in Enantioselective Deprotonation of Epoxides. The Journal of Organic Chemistry 61:18, pages 6108-6113.
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Debnath Bhuniya, Arpita Datta Gupta & Vinod K. Singh. (1995) Synthesis of versatile intermediates for cyclopentanoid natural products via enantioselective deprotonation of substituted cyclopentene oxide. Tetrahedron Letters 36:16, pages 2847-2850.
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Sushil Raina & Vinod K. Singh. (1995) Reaction of epoxides with activated DMSO reagent. General method for synthesis of α-chlorocarbonyl compounds: Application in asymmetric synthesis of (3S)-2,3-oxidosqualene. Tetrahedron 51:8, pages 2467-2476.
Crossref
D. BHUNIYA & V. K. SINGH. (2010) ChemInform Abstract: Enantioselective Deprotonation of Cyclohexene Oxide to (R)‐2‐ Cyclohexen‐1‐ol.. ChemInform 25:48.
Crossref
Arpita Datta Gupta, Debnath Bhuniya & Vinod K. Singh. (1994) Synthesis of homochiral bis (oxazolinyl) pyridine type ligands for asymmetric cyclopropanation reactions. Tetrahedron 50:48, pages 13725-13730.
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