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Synthesis 2004(13): 2075-2090  
DOI: 10.1055/s-2004-831169
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis Using Diastereotopic Groups

Reinhard W. Hoffmann*
Fachbereich Chemie, Philipps Universität Marburg, Hans Meerwein Str., 35032 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: rwho@chemie.uni-marburg.de;
Further Information

Publication History

Received 26 May 2004
Publication Date:
13 August 2004 (online)

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Abstract

Two constitutionally identical but topologically different groups in a chiral molecule are diastereotopic. Selective modification of one of these groups creates one or several new stereogenic centres. This method of stereoselective synthesis that has been used on several occasions is reviewed here. The intention is to focus on an area of stereoselective synthesis that is still underdeveloped.

1 Introduction

2 Intramolecular Differentiation of Diastereotopic Groups

2.1 Diastereotopic Hydroxymethylene Groups

2.2 Diastereotopic Carbonyl Groups

2.3 Diastereotopic Enone Groups

2.4 Diastereotopic Alkene Groups

2.5 Diastereotopic Alkyne Groups

2.6 Diastereotopic Aryl or Alkyl Groups

2.7 Diastereotopic Hydrogen Atoms

2.8 Diastereotopic Halogen Atoms

2.9 Diastereotopic Groups in Pseudo-C2-symmetric Substrates

3 Intermolecular Differentiation of Diastereotopic Groups

3.1 Diastereotopic Methyl Groups

3.2 Diastereotopic Halomethyl Groups

3.3 Diastereotopic Thiomethyl Groups

3.4 Diastereotopic Enone Groups

3.5 Diastereotopic Halogen Atoms

3.6 Diastereotopic Phenylseleno Groups

3.7 Diastereotopic Hydrogen Atoms

3.8 Diastereotopic Groups in Pseudo-C2-symmetric Substrates

4 Conclusion

Key words

asymmetric induction - stereoselective synthesis - dia­stereotopic groups