Enantioselective aldol reactions using homochiral lithium amides as non-covalently bound chiral auxiliaries.
โ Scribed by Yannick Landais; Philippe Ogay
- Book ID
- 103976960
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 330 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0957-4166
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โฆ Synopsis
Syn and axtl aldols have been prepared from ketones and esters respectively with relatively high enantiomeric excesses, using a homochiral lithium amide possessing two coordinating sites, as non-covalently bound chiral auxiliary. The interest in HomoChiral Lithium Amides (HCLAs) as either bases in asymmetric deprotonations, or as non-covalently bound chiral auxiliaries in aldol reactions, has steadily increased.' Although high enantioselectivities can be achieved using traditional covalently bound chiral auxiliaries, recent reports show that use&d enantioselectivities can be obtained using HCLAs. However, to date few mvestigations have been undertaken about the enantioselectivities of HCLA mediated asymmetric aldol reactions using "convertible' carbonyls which have the potential to be fimctionalised after the aldol reaction.* We report herein our preliminary results concerning the asymmetric aldol reactions using Heathcock's versatile carbonyl substrates,3 and two new HCLA bases possessing two co-ordinating groups (OMe). The studies of Kogaa and Shioiri*b-c have shown that high selectivities can be obtained by using homochiral amines containing l,2-amino-alcohol or I,t-diamino moieties, which are known to efficiently
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