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Ytterbium-catalysed conjugate allylation of alkylidene malonates and enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes

หน่วยงาน Edinburgh Research Archive, United Kingdom

รายละเอียด

ชื่อเรื่อง : Ytterbium-catalysed conjugate allylation of alkylidene malonates and enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes , Enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes
นักวิจัย : Fallan, Charlene
คำค้น : organic chemistry , asymmetric catalysis
หน่วยงาน : Edinburgh Research Archive, United Kingdom
ผู้ร่วมงาน : Lam, Hon , Lusby, Paul , Scottish Funding Council
ปีพิมพ์ : 2555
อ้างอิง : http://hdl.handle.net/1842/7683
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : Ytterbium-Catalyzed Conjugate Allylation of Alkylidene Malonates, Fallan, C.; Quigley, P. F.; Lam, H. W. J. Org. Chem. 2011, 76, 4112−4118. , Enantioselective Nickel-Catalyzed Michael Additions of Azaarylacetates and Acetamides to Nitroalkenes, Fallan, C.; Lam, H. W.; Chem. Eur. J. 2012, Chem. Eur. J. 2012, 18, 11214 – 11218.
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

I. Catalytic Conjugate Allylation of Alkylidene Malonates Nucleophilic conjugate addition of allylsilanes and allylstannanes to alkylidene malonates under the action of ytterbium catalysis in the presence of hexafluoro-isopropanol has been developed. Enantioselective conjugate allylation of alkylidene malonates under ytterbium or scandium catalysis using chiral bis(oxazoline) ligands allows access to the conjugate addition products in an enantiomerically-enriched form. Furthermore, elaboration of the allylated substrates via decarboxylation and an oxidative cleavage was demonstrated. II. Catalytic Enantioselective Conjugate Addition of Azaarylacetates and Acetamides to Nitroalkenes An enantioselective nickel-catalysed Michael addition of azaarylacetates and acetamides to nitroalkenes has been developed. A range of azaaryl pronucleophiles were shown to react with a variety of nitroalkenes to generate highly functionalised Michael addition products with impressive diastereo- and enantiocontrol. A possible mechanism for this process is proposed and crystal structures of the addition products have also been attained, allowing determination of the absolute stereochemistry. Elaboration and further functionalisation of these products was also possible under a range of conditions.

บรรณานุกรม :
Fallan, Charlene . (2555). Ytterbium-catalysed conjugate allylation of alkylidene malonates and enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes.
    กรุงเทพมหานคร : Edinburgh Research Archive, United Kingdom .
Fallan, Charlene . 2555. "Ytterbium-catalysed conjugate allylation of alkylidene malonates and enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes".
    กรุงเทพมหานคร : Edinburgh Research Archive, United Kingdom .
Fallan, Charlene . "Ytterbium-catalysed conjugate allylation of alkylidene malonates and enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes."
    กรุงเทพมหานคร : Edinburgh Research Archive, United Kingdom , 2555. Print.
Fallan, Charlene . Ytterbium-catalysed conjugate allylation of alkylidene malonates and enantioselective nickel-catalysed Michael additions of azaarylacetates and acetamides to nitroalkenes. กรุงเทพมหานคร : Edinburgh Research Archive, United Kingdom ; 2555.