Elsevier

Tetrahedron

Volume 56, Issue 17, 21 April 2000, Pages 2561-2576
Tetrahedron

Tetrahedron Report Number 523
The Synthesis of Vicinal Amino Alcohols

https://doi.org/10.1016/S0040-4020(00)00149-6Get rights and content

Introduction

The vicinal amino alcohol moiety is a common structural component in a vast group of naturally occurring and synthetic molecules. The common name for this group varies, from vicinal amino alcohol, to β-amino alcohol, to 1,2-amino alcohol. Either the amine or the alcohol can be acylated, alkylated or contained within rings. The presence of this moiety and the relative (as well as absolute) stereochemistry are generally important for the biological activity of molecules containing a vicinal amino alcohol. As such, a variety of stereoselective synthetic methods have been developed. This review will focus on methods that have been developed for the synthesis of vicinal amino alcohols.

Section snippets

Molecules Containing a Vicinal Amino Alcohol

While the focus of this review is the synthesis of the vicinal amino alcohol moiety, it seems appropriate to provide some background information on the types of molecules containing this grouping of functionality. Three general groups of vicinal amino alcohols have been reported in the literature: (1) naturally occurring molecules containing vicinal amino alcohols; (2) synthetic pharmacologically active molecules containing vicinal amino alcohols; (3) catalysts containing vicinal amino alcohols.

Synthetic Routes to Vicinal Amino Alcohols

Just as there are many examples of molecules containing the vicinal amino alcohol moiety, there are an equally large number of synthetic routes to these molecules (Fig. 8). We cannot be comprehensive in this review and list every method, but will show several examples that typify the main disconnections used to prepare vicinal amino alcohols. Conceptually one can divide these syntheses into four different classes: (1) functional group manipulation of a molecule containing both heteroatoms; (2)

Conclusions

Clearly there are numerous routes to the vicinal amino alcohol moiety, only a broad overview of which has been presented in this review. The choice of synthetic route for a given application will vary depending upon substitution, as well as the relative and/or absolute stereochemistry desired. A key theme in many methods presented here is the generation of enantiomerically pure compounds. This is done via enantiomerically pure starting material as well as chiral catalysis.

There are still many

Acknowledgements

I would like to thank my coworkers (Dionne M. Stanchina, Kristjan M. Arason and Jeffrey A. Frick (Illinois Wesleyan Univ.)) who have both helped with this review as well as carried out our work in the area of amino alcohol synthesis. I would also like to thank the donors of the Petroleum Research Fund, administered by the American Chemical Society, for partial support of this work, PRF31875-G1.

Stephen Bergmeier was born and raised in south-eastern Iowa and attended Iowa State University, graduating with a BS in chemistry in 1981. While there he carried out research with and was introduced to organic synthesis by Prof. George A. Kraus. After Iowa State he attended the University of Nebraska and obtained a Masters degree in organic chemistry, working with Prof. Ray Funk. Following this, he obtained employment at Parke–Davis Pharmaceutical Research in Ann Arbor, Michigan. He then went

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References (141)

  • H. Nakamura et al.

    Antibiot.

    (1976)
  • C.E. O'Connell et al.

    Bioorg. Med. Chem. Lett.

    (1999)
  • B. Wagner et al.

    Bioorg. Med. Chem.

    (1999)
  • Y. Shimojima et al.

    Tetrahedron

    (1984)
  • Y. Shimojima et al.

    Tetrahedron Lett.

    (1982)
  • Y.A. Hannun et al.

    Biochem. Biophys. Acta

    (1993)
  • A.P. Grollman et al.

    J. Biol. Chem.

    (1967)
  • S. Kobayashi et al.

    Tetrahedron Lett.

    (1999)
  • H.M. Crane et al.

    Bioorg. Med. Chem. Lett.

    (1995)
  • J.M. Heerding et al.

    Bioorg. Med. Chem. Lett.

    (1995)
  • A.D. Rodriguez et al.

    Tetrahedron Lett.

    (1996)
  • S.-K. Chung et al.

    Tetrahedron: Asymmetry

    (1999)
  • P. Castejon et al.

    Tetrahedron

    (1996)
  • B.L. Chng et al.

    Bioorg. Med. Chem. Lett.

    (1997)
  • M. Pasto et al.

    Tetrahedron: Asymmetry

    (1995)
  • P. Van de Weghe et al.

    Tetrahedron Lett.

    (1995)
  • X.-L. Hou et al.

    Tetrahedron: Asymmetry

    (1998)
  • U.M. Lindstrom et al.

    Tetrahdron Lett.

    (1997)
  • D. Albanese et al.

    Tetrahedron

    (1997)
  • Q. Liu et al.

    Tetrahedron

    (1997)
  • I. Erden
  • W.H. Pearson et al.
  • N.-S. Kim et al.

    Tetrahedron Lett.

    (1994)
  • T.J. Hodgkinson et al.

    Tetrahedron

    (1998)
  • T. Ibuka et al.

    Tetrahedron

    (1996)
  • G. Cardillo et al.

    Tetrahedron Lett.

    (1997)
  • G.M. Coppola et al.

    Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids

    (1987)
  • S.C. Bergmeier et al.

    J. Org. Chem.

    (1999)
  • H. Umezawa et al.

    J. Antibiot.

    (1976)
  • K. Ino et al.

    Anticancer Res.

    (1995)
  • K. Stratmann et al.

    J. Org. Chem.

    (1994)
  • M. Haddad et al.

    Synlett

    (1999)
  • T.Q. Dinh et al.

    J. Org. Chem.

    (1997)
  • Y. Shimojima et al.

    J. Med. Chem.

    (1985)
  • Y. Shimojima et al.

    J. Med. Chem.

    (1983)
  • Y. Shimojima et al.

    Agric. Biol. Chem.

    (1982)
  • H. Kotsuki et al.

    Org. Lett.

    (1999)
  • K. Shinozaki et al.

    Chem. Pharm. Bull.

    (1996)
  • R.A. Ward et al.

    Tetrahedron

    (1995)
  • P.M. Koskinen et al.

    Synthesis

    (1998)
  • T. Kamiyama et al.

    J. Antibiot.

    (1995)
  • J.F. Bagii et al.

    J. Org. Chem.

    (1973)
  • D. Kluepfel et al.

    J. Antibiot.

    (1972)
  • J. Kobayashi et al.

    J. Chem. Soc., Perkin Trans. 1

    (1991)
  • J.P. Schaefer et al.

    J. Org. Chem.

    (1968)
  • J.P. Schaefer et al.

    J. Chem. Soc., Chem. Commun.

    (1967)
  • A.-W.R. He et al.

    Anticancer Res.

    (1999)
  • J.B. Koepfli et al.

    J. Am. Chem. Soc.

    (1950)
  • S.M. Colegate et al.

    Aust. J. Chem.

    (1979)
  • R.J. Molyneux et al.

    Science

    (1982)
  • Cited by (887)

    View all citing articles on Scopus

    Stephen Bergmeier was born and raised in south-eastern Iowa and attended Iowa State University, graduating with a BS in chemistry in 1981. While there he carried out research with and was introduced to organic synthesis by Prof. George A. Kraus. After Iowa State he attended the University of Nebraska and obtained a Masters degree in organic chemistry, working with Prof. Ray Funk. Following this, he obtained employment at Parke–Davis Pharmaceutical Research in Ann Arbor, Michigan. He then went across the road to the University of Michigan to obtain a Ph.D in medicinal chemistry under the direction of Prof. William H. Pearson. Postdoctoral research was done in the laboratories of Prof. Henry Rapoport at the University of California, Berkeley. His first independent position was as an assistant professor in the Division of Medicinal Chemistry and Pharmacognosy in the College of Pharmacy at Ohio State University. While there he has investigated the use of aziridines for the synthesis of vicinal amino alcohols among other targets. He is also working on the development of novel oligonucleotide analogues and the design and synthesis of novel nicotinic antagonists. As of July 1, 2000, he will be an associate professor in the Department of Chemistry and Biochemistry at Ohio University in Athens, Ohio.

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