Abstract
With modern methods for asymmetric catalysis breaking ground, the use of chiral auxiliaries
seems to be old-fashioned and rather inefficient. However, for many transformations,
chiral auxiliaries often represent the only selective method available. In addition,
high levels of selectivity and reliability are often attractive characteristics of
chiral auxiliaries and allow for the efficient and rapid synthesis of desired chiral
compounds. In addition, even in cases with imperfect selectivity, the use of an attached
chiral auxiliary allows the enrichment of diastereoselectivity, and hence enantioselectivity
after removal of the auxiliary, by many standard separation techniques. This article
gives an overview on the most important classes of chiral auxiliaries, discussing
the mode of action and highlighting some recent applications. It does not deal with
the use of chiral catalysts, chiral reagents or achiral auxiliaries.
-
1 Introduction
-
2 Sulfinamides, Sulfoxides, Bis(sulfoxides)
-
3 Camphor-Derived Auxiliaries
-
4 Carbohydrate-Derived Auxiliaries
-
5 RAMP, SAMP
-
6 Alcohols, Amines, Amino Alcohols
-
7 Oxazolidinones, Oxazolines, Oxazolidines
-
8 Conclusion
Key words
asymmetric synthesis - chiral auxiliary - diastereoselectivity - sulfoxides - oxazolidinones
- SAMP
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