Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary α-hydroxy phosphonates

• Published in: Tetrahedron Vol. 67; no. 19; pp. 3464 - 3469
• Main Authors: Seven, Ozlem, Polat-Cakir, Sidika, Hossain, Md. Shakhawoat, Emrullahoglu, Mustafa, Demir, Ayhan S.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 13.05.2011; Elsevier
• Subjects: Acyl phosphonates; Chemistry; Chemistry, Organic; Exact sciences and technology; Organic chemistry; Organoaluminum; Organometalloidal and organometallic compounds; P derivatives; Physical Sciences; Preparations and properties; Science & Technology; α-Hydroxy phosphonates; α-Hydroxy phosphonates; Acyl phosphonates; Organoaluminum; QRSSPHHBVAJLAM-UHFFFAOYSA-N; ASYMMETRIC-SYNTHESIS; ACIDS; ANALOGS; ALDEHYDES; ENANTIOSELECTIVE ADDITION; alpha-Hydroxy phosphonates; HIV PROTEASE; ACYLPHOSPHONATES; INHIBITORS; ANION EQUIVALENTS; PROTEIN-TYROSINE-PHOSPHATASE; Chemical reagent; Aromatic compound; Organic phosphonate; Aluminium Organic compounds; Chemical synthesis; Ketone; Phosphorus Organic compounds
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.03.036

The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of α-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary α-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 °C gave the secondary α-hydroxy phosphonates, while at −100 °C they afford the tertiary α-hydroxy phosphonates. [Display omitted]