Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates
TETRAHEDRON, vol.67, no.19, pp.3464-3469, 2011 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 67 Issue: 19
- Publication Date: 2011
- Doi Number: 10.1016/j.tet.2011.03.036
- Journal Name: TETRAHEDRON
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.3464-3469
- Keywords: Acyl phosphonates, Organoaluminum, alpha-Hydroxy phosphonates, PROTEIN-TYROSINE-PHOSPHATASE, ENANTIOSELECTIVE ADDITION, ASYMMETRIC-SYNTHESIS, ANION EQUIVALENTS, HIV PROTEASE, INHIBITORS, ALDEHYDES, ACIDS, ACYLPHOSPHONATES, ANALOGS
- Open Archive Collection: AVESIS Open Access Collection
- Middle East Technical University Affiliated: Yes
Abstract
The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of alpha-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary alpha-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 degrees C gave the secondary alpha-hydroxy phosphonates, while at -100 degrees C they afford the tertiary alpha-hydroxy phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.