Abstract
Complementary approaches under enolate amination reactions for the synthesis of both α-hydrazidoacyl diastereomers have been achieved. Both isomers are obtained with high to excellent chemical yields and high stereoselectivities (up to >95:5 dr) when aryl-substituted camphor N1-acyl N2-phenylpyrazolidinone was treated with potassium hexamethyldisilylamide (KHMDS) and lithium hexamethyldisilylamide (LHMDS), respectively, followed by the addition of di-tert-butyl azodicarboxylate. The nondestructive removal of the chiral auxiliary, which can be carried out under mild condition, afforded the hydrazido alcohol with high enantiomeric ratio. The facial stereoselectivity and stereochemical course of the reactions are discussed.
Original language | English |
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Pages (from-to) | 333-336 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 50 |
Issue number | 3 |
DOIs | |
Publication status | Published - 2009 Jan 21 |
Keywords
- Amination
- Chiral auxiliary
- Reversal of stereoselectivity
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Dive into the research topics of 'Diastereoselective electrophilic α-amination of camphor N1-acyl N2-phenylpyrazolidinones: the metal enolate-dependent synthesis of two possible hydrazide diastereomers'. Together they form a unique fingerprint.Datasets
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CCDC 723366: Experimental Crystal Structure Determination
Chao, C. (Creator), Cheng, C. (Creator), Li, S. (Creator) & Chen, K. (Creator), Unknown Publisher, 2009
DOI: 10.5517/ccs8qd4, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccs8qd4&sid=DataCite
Dataset
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CCDC 723364: Experimental Crystal Structure Determination
Chao, C. (Creator), Cheng, C. (Creator), Li, S. (Creator) & Chen, K. (Creator), Unknown Publisher, 2009
DOI: 10.5517/ccs8qb2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccs8qb2&sid=DataCite
Dataset
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CCDC 723362: Experimental Crystal Structure Determination
Chao, C. (Creator), Cheng, C. (Creator), Li, S. (Creator) & Chen, K. (Creator), Unknown Publisher, 2009
DOI: 10.5517/ccs8q80, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccs8q80&sid=DataCite
Dataset