Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine Nitroxide Radical via Combined Iterative Nucleophilic Additions and Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones
A sterically hindered bis-spirocyclic C-2-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an L-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two alpha-carbon atoms has been accomplishe...
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| Published in | Journal of organic chemistry Vol. 77; no. 23; pp. 10688 - 10698 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
Amer Chemical Soc
07.12.2012
American Chemical Society |
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| Abstract | A sterically hindered bis-spirocyclic C-2-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an L-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two alpha-carbon atoms has been accomplished through iteration of completely regio- and stereoselective intramolecular cycloaddition reactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation procedures. This method appears to be very useful for building up bulky spirocyclic moieties adjacent to a nitroxide group and provides an important supplementation to traditional methods of nitroxide synthesis. The synthesized chiral nitroxide showed a very high stability to reduction with ascorbate (k approximate to 8 x 10(-3) M-1 s(-1)). |
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| AbstractList | A sterically hindered bis-spirocyclic C(2)-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an l-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two α-carbon atoms has been accomplished through iteration of completely regio- and stereoselective intramolecular cycloaddition reactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation procedures. This method appears to be very useful for building up bulky spirocyclic moieties adjacent to a nitroxide group and provides an important supplementation to traditional methods of nitroxide synthesis. The synthesized chiral nitroxide showed a very high stability to reduction with ascorbate (k ≈ 8 × 10(-3) M(-1) s(-1)).A sterically hindered bis-spirocyclic C(2)-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an l-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two α-carbon atoms has been accomplished through iteration of completely regio- and stereoselective intramolecular cycloaddition reactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation procedures. This method appears to be very useful for building up bulky spirocyclic moieties adjacent to a nitroxide group and provides an important supplementation to traditional methods of nitroxide synthesis. The synthesized chiral nitroxide showed a very high stability to reduction with ascorbate (k ≈ 8 × 10(-3) M(-1) s(-1)). A sterically hindered bis-spirocyclic C(2)-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an l-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two α-carbon atoms has been accomplished through iteration of completely regio- and stereoselective intramolecular cycloaddition reactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation procedures. This method appears to be very useful for building up bulky spirocyclic moieties adjacent to a nitroxide group and provides an important supplementation to traditional methods of nitroxide synthesis. The synthesized chiral nitroxide showed a very high stability to reduction with ascorbate (k ≈ 8 × 10(-3) M(-1) s(-1)). A sterically hindered bis-spirocyclic C₂-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an l-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two α-carbon atoms has been accomplished through iteration of completely regio- and stereoselective intramolecular cycloaddition reactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation procedures. This method appears to be very useful for building up bulky spirocyclic moieties adjacent to a nitroxide group and provides an important supplementation to traditional methods of nitroxide synthesis. The synthesized chiral nitroxide showed a very high stability to reduction with ascorbate (k ≈ 8 × 10–³ M–¹ s–¹). A sterically hindered bis-spirocyclic C-2-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an L-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two alpha-carbon atoms has been accomplished through iteration of completely regio- and stereoselective intramolecular cycloaddition reactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation procedures. This method appears to be very useful for building up bulky spirocyclic moieties adjacent to a nitroxide group and provides an important supplementation to traditional methods of nitroxide synthesis. The synthesized chiral nitroxide showed a very high stability to reduction with ascorbate (k approximate to 8 x 10(-3) M-1 s(-1)). |
| Author | Morozov, Denis A. Bagryanskaya, Irina Yu Goti, Andrea Kuratieva, Natalia V. Komarov, Denis A. Grigor'ev, Igor A. Kirilyuk, Igor A. |
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| Cites_doi | 10.1055/s-0030-1260933 10.1021/ja210315x 10.1002/chem.200900707 10.1016/S0040-4039(03)00239-9 10.1002/mrm.10312 10.1002/ejoc.200300608 10.1021/ol015747o 10.1055/s-2007-991059 10.1021/cr990119u 10.1021/jo061130e 10.1002/ejoc.200801255 10.1002/chem.201001608 10.1016/j.tet.2010.02.004 10.1021/ol035798g 10.1021/ma0012752 10.1002/chem.200903102 10.1016/j.freeradbiomed.2006.11.007 10.1016/j.tetlet.2004.12.119 10.1021/jo101961m 10.1055/s-2008-1078445 10.1016/j.tetlet.2004.09.050 10.1002/chem.200801578 10.1007/s00723-010-0179-z 10.1039/b903904j 10.1016/j.freeradbiomed.2007.02.030 10.1055/s-2004-834937 10.1021/jo0509408 10.1002/ejoc.200800098 10.1080/10715760902914575 10.1002/chem.200305427 10.1039/b400252k 10.1080/15257770701572055 10.1080/10715760701449302 10.1021/ma050343n 10.1002/ejoc.201000632 |
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| Keywords | STABLE FREE-RADICALS REGIOSELECTIVE OXIDATION ISOXAZOLIDINES X=Y-ZH SYSTEMS DIASTEREOSELECTIVE SYNTHESIS REDUCTION POTENTIAL 1,3-DIPOLES STEREOSELECTIVE-SYNTHESIS N-OXIDES EN-ROUTE |
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| Snippet | A sterically hindered bis-spirocyclic C-2-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an L-tartaric derived... A sterically hindered bis-spirocyclic C(2)-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an l-tartaric derived... A sterically hindered bis-spirocyclic C₂-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an l-tartaric derived... |
| Source | Web of Science |
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| StartPage | 10688 |
| SubjectTerms | Chemistry Chemistry, Organic cycloaddition reactions Lewis bases moieties organic chemistry oxidation Physical Sciences Science & Technology stereoselectivity |
| Title | Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine Nitroxide Radical via Combined Iterative Nucleophilic Additions and Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones |
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| Volume | 77 |
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