Stereocontrolled α-Alkylation of Oxime Ether Derived from Terpene: Efficient Synthesis of New Chiral γ- and δ-Amino Alcohols

Thomas Jennequin; Stéphane Labat; Loïc Toupet; Jean-Claude Caille; Marc Mauduit

doi:10.1055/s-2008-1078492

LETTER

Stereocontrolled α-Alkylation of Oxime Ether Derived from Terpene: Efficient Synthesis of New Chiral γ- and δ-Amino Alcohols

Thomas Jennequin^a, Stéphane Labat^a, Loïc Toupet^b, Jean-Claude Caille*^c, Marc Mauduit*^a
^a ‘Sciences Chimiques de Rennes’, UMR 6226 CNRS - Equipe Chimie Organique et Supramoléculaire - Ecole Nationale Supérieure de Chimie de Rennes, Avenue du Général Leclerc, 35700 Rennes, France
e-Mail: marc.mauduit@ensc-rennes.fr;
^b Groupe Matière Condensée et Matériaux, UMR CNRS 6626, Avenue du General Leclerc CS 74205, 35042 Rennes, France
^c Zambon ZI la Croix-Cadeau, B.P. 10079, 49243 Avrillé, France
e-Mail: jean-claude.caille@zambongroup.com;

Abstract

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Abstract

The alkylation of (+)-nopinone oxime ether with various electrophiles afforded the corresponding adduct with a total stereoselectivity. Further reduction of the oxime ether afforded an easily access to new chiral γ-and δ-amino alcohols of high interest for catalysis and asymmetric synthesis.

Key words

oxime ether - (+)-nopinone - stereocontrolled alkylation - amino alcohols

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References

References and Notes

<A NAME="RG09808ST-1">1</A> Shue H.-J. Chen X. Schwerdt JH. Paliwal S. Blythin DJ. Lin L. Gu D. Wang C. Reichard GA. Wang H. Piwinski JJ. Duffy RA. Lachowicz JE. Coffin VL. Nomeir AA. Morgan CA. Varty GB. Shih N.-Y. Bioorg. Med. Chem. Lett. 2006, 16: 1065

<A NAME="RG09808ST-2A">2a</A> Shu Y. Liu D. Sun N. J. Org. Chem. 2006, 44: 3998

<A NAME="RG09808ST-2B">2b</A> Huang X. Ortiz-Marciales M. Huang K. Stepanenko V. Merced FG. Ayala AM. Correa W. De Jesús M. Org. Lett. 2007, 9: 1793

<A NAME="RG09808ST-3A">3a</A> Czekelius C. Carreira EM. Angew. Chem. Int. Ed. 2005, 44: 612

<A NAME="RG09808ST-3B">3b</A> Narsaiah AV. Nagaiah K. Adv. Synth. Catal. 2004, 346: 1271

<A NAME="RG09808ST-3C">3c</A> Anand N. Owston NA. Parker AJ. Slatford PA. Williams JMJ. Tetrahedron Lett. 2007, 48: 7761

<A NAME="RG09808ST-4A">4a</A> Bartlett PA. McLaren KL. Ting PC. J. Am. Chem. Soc. 1988, 110: 1634

<A NAME="RG09808ST-4B">4b</A> For a review, see: Miyabe H. Ueda M. Naito T. Synlett 2004, 1140

<A NAME="RG09808ST-5A">5a</A> Shatzmiller S. Bahar E. Bercovici S. Cohen A. Verdoorn G. Synthesis 1990, 502

<A NAME="RG09808ST-5B">5b</A> Lidor R. Shatzmiller S. J. Am. Chem. Soc. 1981, 103: 5916

<A NAME="RG09808ST-5C">5c</A> Shatzmiller S. Dolitzki B.-Z. Liebigs Ann. Chem. 1991, 189

<A NAME="RG09808ST-5D">5d</A> Shatzmiller S. Bercovici S. J. Chem. Soc., Chem. Commun. 1990, 327

<A NAME="RG09808ST-6A">6a</A> Gallagher PT. Hunt JCA. Lightfoot AP. Moody CJ. J. Chem. Soc., Perkin Trans. 1 1997, 2633

<A NAME="RG09808ST-6B">6b</A> Hunt JCA. Laurent P. Moody CJ. J. Chem. Soc., Perkin Trans. 1 2002, 2378

Crystallographic data for the structural have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 665258, 298980, and 653068 for compounds 9a, 11c, and 10o, respectively. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk].

<A NAME="RG09808ST-8">8</A> Campos KR. Journet M. Cai D. Kowal JJ. Lee S. Larsen RD. Reider PJ. J. Org. Chem. 2003, 68: 2338

<A NAME="RG09808ST-9A">9a</A> Tsuri T. Honma T. Hiramatsu Y. Mitsumori S. Inagaki M. Arimura A. Yasui K. Asanuma F. Kishino J. Ohtani M. J. Med. Chem. 1997, 40: 3504

<A NAME="RG09808ST-9B">9b</A> Seno K. Hagashita S. Chem. Pharm. Bull. 1989, 37: 1524

<A NAME="RG09808ST-10">10</A> Lait SM. Rankic DA. Keavy BA. Chem. Rev. 2007, 107: 767

<A NAME="RG09808ST-11">11</A> Cordova A. Sunden H. Xu Y. Ibrahem I. Zou W. Engqvist M. Chem. Eur. J. 2006, 12: 5446