Synthesis of analogues of 5-iodo-2′-deoxyuridine-5′-diphosphate

Jennings, L. J.; Macchia, Marco; Parkin, A.

doi:10.1039/p19920002197

Cited by 33 publications

(23 citation statements)

References 35 publications

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“…With 5 mol% TiA C H T U N G T R E N N U N G (O-i-Pr) 4 , the corresponding product was obtained with 58% isolated yield for 12 h. In contrast, other Lewis acids which were effective for the hydrophosphonylation of aldehydes or aldimines gave 3a with 16% yield ( An intensive investigation of the reaction conditions revealed that the concentration of acetophenone played a crucial role on the reactivity (Figure 1). [15b] By increasing the concentration of acetophenone, the yield was dramatically improved.…”

Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 98%

“…The tridentate Schiff base 6- 4 complex catalyzed the asymmetric hydrophosphonylation of acetophenone smoothly under neat conditions, giving the corresponding quaternary a-hydroxy phosphonate in high yield with 55% ee.…”

Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 99%

“…A preliminary survey revealed that the mildly acidic TiA C H T U N G T R E N N U N G (O-i-Pr) 4 was a promising catalyst for the hydrophosphonylation of acetophenone (Table 1, entry 1). With 5 mol% TiA C H T U N G T R E N N U N G (O-i-Pr) 4 , the corresponding product was obtained with 58% isolated yield for 12 h. In contrast, other Lewis acids which were effective for the hydrophosphonylation of aldehydes or aldimines gave 3a with 16% yield ( An intensive investigation of the reaction conditions revealed that the concentration of acetophenone played a crucial role on the reactivity (Figure 1).…”

Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 99%

“…2009, 351, 2567-2572 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim asc.wiley-vch.de tion of ketones was highly tolerable for functional ketones (products 3t-v). In particular, the mild acidity of TiA C H T U N G T R E N N U N G (O-i-Pr) 4 made it an effective catalyst for the reaction of ketone 1s, which contained an acid-sensitive…”

Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 99%

“…The a-hydroxy phosphonates have exhibited intriguing biological activities, [1] and are widely applied in pharmaceutical chemistry as bio-phosphate mimics, [2] antibiotics, [3] anti-virals [4] and anti-tumour agents. [5] Particularly, as analogues of quaternary a-hydroxy acids, the quaternary a-hydroxy phosphonates are of considerable value because they may potentially increase the rigidity and resistance to protease enzymes and enhance bioactivity.…”

Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 99%

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Highly Efficient Synthesis of Quaternary α‐Hydroxy Phosphonates via Lewis Acid‐Catalyzed Hydrophosphonylation of Ketones

et al. 2009

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A Lewis acid catalyst has been first applied to the hydrophosphonylation of ketones, giving the corresponding quaternary a-hydroxy phosphonates in high yields (up to 98%). The present method was highly tolerable for functionalized ketones. Moreover, the first catalytic enantioselective hydrophosphonylation of an unactivated ketone was also realized by using a tridentate Schiff base-titanium complex.

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Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 98%

Section: Highly Efficient Synthesis Of Quaternary A-hydroxymentioning

confidence: 99%