Preparation of α-ketophosphonates by a [3,3]-sigmatropoic shift of enolphosphonates

Afarinkia, K.; Twist, Andrew; Yu, Hiu-wan

doi:10.1016/j.jorganchem.2004.10.016

Cited by 8 publications

(3 citation statements)

References 19 publications

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“…Oxidative cleavage of 3b and 4b provided aldehydes 3c and 4c (Scheme ) along with the desired lactones 3d and 4d as minor products in 6:1 ratio in AcOEt or CH 2 Cl 2 (Table , entries 7 and 9). This result is in accord with the higher reactivity of acyl phosphonates at the C center than the P center ,, and with Whitesides’ and Chan’s results …”

supporting

confidence: 89%

Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

2008

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supporting

confidence: 89%

Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

2008

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“…L'alkylation des a-ce ´tophosphonates en a de la fonction carbonyle, est possible gra ˆce a `un processus en deux e ´tapes qui commence par une O-alkylation et se termine par un re ´arrangement [3,3] sigmatropique. La premie `re e ´tape est ste ´re ´ospe ´cifique et conduit exclusivement a `l'isome `re E [113,114] (Sche ´ma 106).…”

Section: Re ´Arrangement [33] Sigmatropiqueunclassified

Synthèses et applications des oxophosphonates en chimie organique

Atmani

Memmou

Bouillon

2009

Comptes Rendus. Chimie

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Re ´sume Ćetravail consacre ´aux oxophosphonates, concerne trois classes de produits : les a-ce ´tophosphonates, les b-ce ´tophosphonates, et enfin les get d-ce ´tophosphonates que nous avons regroupe ´s en une seule classe. Pour chaque classe, nous avons e ´voque ĺes diffe ´rentes me ´thodes de synthe `se ainsi que leur re ´activite ´. Dans cette dernie `re partie, nous avons de ´veloppe ´les diffe ´rentes me ´thodes de re ´duction, les re ´actions d'addition nucle ´ophile et les re ´actions de substitution par les he ´te ´roatomes. Nous avons particulie `rement mis l'accent sur les de ´rive ´s soufre ´s et amine ´s et les de ´rive ´s fluore ´s et chlore ´s.

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“…13 Previously, Jørgensen and coworkers also used β,γ-unsaturated α-ketophosphonates as surrogates of α,β-unsaturated esters/amides in an organocatalyzed Michael reaction. 14 Most recently, we successfully realized the first direct application of acetylphosphonate as an enolate precursor 15 in Brønsted base-catalyzed aldol reactions.…”

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confidence: 99%

Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes

Guang

Zhao

2013

Tetrahedron Letters

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The first enantioselective Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes has been brealized by using a new bifunctional Takemoto-type thiourea catalyst. The primary Michael adducts obtained were converted in situ to the corresponding amides through the aminolysis. High yields, excellent diastereoselectivities (>95:5 dr), and good enantioselectivities (up to 81% ee) have been achieved for the corresponding α ,β-disubstituted γ-nitroamides. This reaction againdemon strated that α-ketophosphonates are interesting pronucleophiles that can be used as amide surrogates in organocatalyzed reactions.

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Preparation of α-ketophosphonates by a [3,3]-sigmatropoic shift of enolphosphonates

Cited by 8 publications

References 19 publications

Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates

Synthèses et applications des oxophosphonates en chimie organique

Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes

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