IRIS publication 279269068
Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form gamma-lactams
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TY - JOUR - Clarke, LA,Ring, A,Ford, A,Sinha, AS,Lawrence, SE,Maguire, AR - 2014 - December - Organic ; Biomolecular Chemistry - Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form gamma-lactams - Validated - WOS: 23 () - ALPHA-DIAZOACETAMIDES INTRAMOLECULAR ADDITION CARBENE INSERTION DIASTEREOSELECTIVITY TRANSFORMATIONS DIAZOSULFONES DIRHODIUM(II) STEREOCONTROL CYCLIZATION SELECTIVITY - 12 - 7612 - 7628 - The first examples of asymmetric copper-catalysed intramolecular C-H insertion reactions of 2-sulfonyl-2-diazoacetamides are described; trans gamma-lactams with up to 82% ee are achieved with the CuCl2-bisoxazoline-NaBARF catalyst system. The reactions generally display high efficiency and high trans selectivity, and also a strong regiochemical preference for insertion to lead to the formation of 5-membered rings over 4-membered rings. In cases where there are competing C-H insertion pathways available, to form sulfolanes or thiopyrans, only the insertion into the amide chain to form gamma-lactams is observed. With phenylsulfonyl derivatives, a minor competing C-H insertion pathway leading to beta-lactams is seen; interestingly, changing the identity of the copper ligand changes the product ratio of beta/gamma-lactams. The copper catalysed reactions compare favorably in terms of efficiency and enantioselectivity to the corresponding reactions catalysed by commercially available chiral rhodium catalysts. - 10.1039/c4ob01430h DA - 2014/12 ER -
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@article{V279269068, = {Clarke, LA and Ring, A and Ford, A and Sinha, AS and Lawrence, SE and Maguire, AR }, = {2014}, = {December}, = {Organic ; Biomolecular Chemistry}, = {Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form gamma-lactams}, = {Validated}, = {WOS: 23 ()}, = {ALPHA-DIAZOACETAMIDES INTRAMOLECULAR ADDITION CARBENE INSERTION DIASTEREOSELECTIVITY TRANSFORMATIONS DIAZOSULFONES DIRHODIUM(II) STEREOCONTROL CYCLIZATION SELECTIVITY}, = {12}, pages = {7612--7628}, = {{The first examples of asymmetric copper-catalysed intramolecular C-H insertion reactions of 2-sulfonyl-2-diazoacetamides are described; trans gamma-lactams with up to 82% ee are achieved with the CuCl2-bisoxazoline-NaBARF catalyst system. The reactions generally display high efficiency and high trans selectivity, and also a strong regiochemical preference for insertion to lead to the formation of 5-membered rings over 4-membered rings. In cases where there are competing C-H insertion pathways available, to form sulfolanes or thiopyrans, only the insertion into the amide chain to form gamma-lactams is observed. With phenylsulfonyl derivatives, a minor competing C-H insertion pathway leading to beta-lactams is seen; interestingly, changing the identity of the copper ligand changes the product ratio of beta/gamma-lactams. The copper catalysed reactions compare favorably in terms of efficiency and enantioselectivity to the corresponding reactions catalysed by commercially available chiral rhodium catalysts.}}, = {10.1039/c4ob01430h}, source = {IRIS} }
Data as stored in IRIS
AUTHORS | Clarke, LA,Ring, A,Ford, A,Sinha, AS,Lawrence, SE,Maguire, AR | ||
YEAR | 2014 | ||
MONTH | December | ||
JOURNAL_CODE | Organic ; Biomolecular Chemistry | ||
TITLE | Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form gamma-lactams | ||
STATUS | Validated | ||
TIMES_CITED | WOS: 23 () | ||
SEARCH_KEYWORD | ALPHA-DIAZOACETAMIDES INTRAMOLECULAR ADDITION CARBENE INSERTION DIASTEREOSELECTIVITY TRANSFORMATIONS DIAZOSULFONES DIRHODIUM(II) STEREOCONTROL CYCLIZATION SELECTIVITY | ||
VOLUME | 12 | ||
ISSUE | |||
START_PAGE | 7612 | ||
END_PAGE | 7628 | ||
ABSTRACT | The first examples of asymmetric copper-catalysed intramolecular C-H insertion reactions of 2-sulfonyl-2-diazoacetamides are described; trans gamma-lactams with up to 82% ee are achieved with the CuCl2-bisoxazoline-NaBARF catalyst system. The reactions generally display high efficiency and high trans selectivity, and also a strong regiochemical preference for insertion to lead to the formation of 5-membered rings over 4-membered rings. In cases where there are competing C-H insertion pathways available, to form sulfolanes or thiopyrans, only the insertion into the amide chain to form gamma-lactams is observed. With phenylsulfonyl derivatives, a minor competing C-H insertion pathway leading to beta-lactams is seen; interestingly, changing the identity of the copper ligand changes the product ratio of beta/gamma-lactams. The copper catalysed reactions compare favorably in terms of efficiency and enantioselectivity to the corresponding reactions catalysed by commercially available chiral rhodium catalysts. | ||
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DOI_LINK | 10.1039/c4ob01430h | ||
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