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
