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Synthesis 2006(12): 1899-1930
DOI: 10.1055/s-2006-942399
DOI: 10.1055/s-2006-942399
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Chiral Auxiliaries - Principles and Recent Applications
Further Information
Received
6 January 2006
Publication Date:
17 May 2006 (online)
Publication History
Publication Date:
17 May 2006 (online)
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.
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1 Introduction
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2 Sulfinamides, Sulfoxides, Bis(sulfoxides)
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3 Camphor-Derived Auxiliaries
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4 Carbohydrate-Derived Auxiliaries
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5 RAMP, SAMP
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6 Alcohols, Amines, Amino Alcohols
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7 Oxazolidinones, Oxazolines, Oxazolidines
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8 Conclusion
Key words
asymmetric synthesis - chiral auxiliary - diastereoselectivity - sulfoxides - oxazolidinones - SAMP
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References
For information about asymmetric additions to C=N double bonds, see refs. 88b and 88c.