Stereoselective Synthesis of Enantioenriched Acetylenic 1,2-Amino Alcohols

Fabrice Chemla; Franck Ferreira; Xavier Gaucher; Laëtitia Palais

doi:10.1055/s-2007-965989

PAPER

Stereoselective Synthesis of Enantioenriched Acetylenic 1,2-Amino Alcohols

Fabrice Chemla, Franck Ferreira*, Xavier Gaucher, Laëtitia Palais
Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Institut de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, 75252 Paris Cedex 05, France
Fax: +33(0)144275571; e-Mail: franck.ferreira@upmc.fr;

Abstract

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Abstract

The stereoselective synthesis of enantioenriched anti- and syn-4-aminoalk-1-yn-3-ols is described. Initial reaction of racemic 3-(methoxymethoxy)allenylzinc with enantiopure Ellman’s (S _S)-(tert-butylsulfinyl)imines was shown to give straightforward and highly stereoselective access to anti-(S _S,3S,4R)-3-(methoxymethoxy)-4-sulfinamidoalk-1-ynes. Upon treatment with dry methanolic hydrochloric acid at reflux, the latter led to the corresponding enantioenriched anti-(3S,4R)-4-aminoalk-1-yn-3-ols. Regarding the syn-diastereomeric (3R,4R)-4-aminoalk-1-yn-3-ols, they were obtained by ring opening of the corresponding cis-N-(tert-butylsulfinyl)aziridines by water under acidic conditions.

Key words

amino alcohols - asymmetric synthesis - chiral auxiliaries - sulfoxides - zinc

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References

1a Bergmeier SC. Tetrahedron 2000, 56: 2561

1b Reetz MT. Chem. Rev. 1999, 99: 1121

2a Yokomatsu Y. Yuasa Y. Shibuya S. Heterocycles 1992, 33: 1051

2b Ohfune Y. Acc. Chem. Res. 1992, 25: 360

2c Reetz MT. Angew. Chem., Int. Ed. Engl. 1991, 30: 1531

3 Golebiowski A. Jurczak J. Synlett 1993, 241

4a Gante J. Angew. Chem., Int. Ed. Engl. 1994, 33: 1699

4b Aoyagi T. Tobe H. Kojima F. Hamada M. Takeuchi T. Umezawa H. J. Antibiot. 1978, 31: 636

4c Umezawa H. Aoyagi T. Suda H. Hamada M. Takeuchi T. J. Antibiot. 1976, 29: 97

4d Umezawa H. Aoyagi T. Morishima H. Matsuzaki M. Hamada M. Takeuchi T. J. Antibiot. 1970, 23: 259

5a Iwamoto RH. Lim P. Bhacca NS. Tetrahedron Lett. 1968, 9: 3891

5b Arcamone F. Cassinelli G. Orezzi P. Franceschi G. Mondelli R. J. Am. Chem. Soc. 1964, 86: 5334

6 Howell AR. So RC. Richardson ST. Tetrahedron 2004, 60: 11327

7 Howarth J. Lloyd DG. J. Antimicrob. Chemother. 2000, 46: 625

8 Stepanenko V. Ortiz-Marciales M. Correa W. De Jesús M. Espinosa S. Ortiz L. Tetrahedron: Asymmetry 2006, 17: 112

9 Ager DJ. Prakash I. Schaad DR. Chem. Rev. 1996, 96: 835

10 Gridley JJ. Coogan MP. Knight DW. Malik KMA. Sharland CM. Singkhonrat J. Williams S. Chem. Commun. 2003, 2550

11a Alemany C. Bach J. Farràs J. Garcia J. Org. Lett. 1999, 1: 1831

11b Dondoni A. Perrone D. Turturici E. J. Org. Chem. 1999, 64: 5557

12a Andrés JM. Pedrosa R. Pérez-Encabo A. Tetrahedron Lett. 2006, 47: 5317

12b Ohno H. Takemoto Y. Fujii N. Ibuka T. J. Chem. Soc., Perkin Trans. 1 1999, 2979

13 Poisson J.-F. Normant JF. Org. Lett. 2001, 3: 1889

14a Chemla F. Ferreira F. Curr. Org. Chem. 2002, 6: 539

14b Chemla F. Bernard N. Ferreira F. Normant J.-F. Eur. J. Org. Chem. 2001, 3295

15a Ferreira F. Audouin M. Chemla F. Chem. Eur. J. 2005, 11: 5269

15b Chemla F. Ferreira F. J. Org. Chem. 2004, 69: 8244

15c Chemla F. Ferreira F. Synlett 2004, 983

15d Ferreira F. Denichoux D. Bejjani J. Chemla F. Synlett 2004, 2051

15e Chemla F. Ferreira F. Hebbe V. Stercklen E. Eur. J. Org. Chem. 2002, 1385

16 Palais L. Chemla F. Ferreira F. Synlett 2006, 1039

17 Chemla F. Ferreira F. Synlett 2006, 2613

18 Kieczykowski GR. Schlessinger RH. J. Am. Chem. Soc. 1978, 100: 1938

19a Weix DJ. Ellman JA. Org. Lett. 2003, 5: 1317

19b Cogan DA. Liu J. Kim K. Backes BJ. Ellman JA. J. Am. Chem. Soc. 1998, 120: 8011

20 Liu J. Cogan DA. Ellman JA. J. Am. Chem. Soc. 1997, 119: 9913

21 Paterson I. Delgado O. Florence GJ. Lyothier I. O’Brien M. Scott JP. Sereinig N. J. Org. Chem. 2005, 70: 150