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Asymmetric synthesis of δ-chloro-β-amino-N-sulfinyl imidates as versatile chiral building blocks for the synthesis of 2,3-disubstituted piperidines

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Abstract
Mannich-type reactions of chiral delta-chloro-N-tert-butanesulfinyl-substituted imidates across N-sulfonyl aldimines resulted in the efficient and anti-stereoselective synthesis of new beta-(sulfonylamino)-N-sulfinyl imidates (dr > 99:1). These compounds were then successfully cyclized to give 2-aryl-N-sulfonylpiperidine-3-(N-sulfinyl) carbimidates in high yields. These proved to be useful intermediates for the synthesis of chiral methyl 2-arylpiperidine-3-carboxylates as well as cis-3-amino-2-aryl-N-sulfonylpiperidines.
Keywords
Chiral auxiliaries, Asymmetric synthesis, Cyclization, Diastereoselectivity, Nitrogen heterocycles, MANNICH-TYPE REACTIONS, ENANTIOSELECTIVE SYNTHESIS, SUBSTANCE-P, TERT-BUTANESULFINAMIDE, MICHAEL ADDITION, DIASTEREOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, NONPEPTIDE ANTAGONIST, ACID-DERIVATIVES, NIPECOTIC ACID

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Citation

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Chicago
Semina, Elena, Filip Colpaert, Kristof Van Hecke, Norbert De Kimpe, and Sven Mangelinckx. 2015. “Asymmetric Synthesis of δ-chloro-β-amino-N-sulfinyl Imidates as Versatile Chiral Building Blocks for the Synthesis of 2,3-disubstituted Piperidines.” European Journal of Organic Chemistry (22): 4847–4859.
APA
Semina, E., Colpaert, F., Van Hecke, K., De Kimpe, N., & Mangelinckx, S. (2015). Asymmetric synthesis of δ-chloro-β-amino-N-sulfinyl imidates as versatile chiral building blocks for the synthesis of 2,3-disubstituted piperidines. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (22), 4847–4859.
Vancouver
1.
Semina E, Colpaert F, Van Hecke K, De Kimpe N, Mangelinckx S. Asymmetric synthesis of δ-chloro-β-amino-N-sulfinyl imidates as versatile chiral building blocks for the synthesis of 2,3-disubstituted piperidines. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2015;(22):4847–59.
MLA
Semina, Elena, Filip Colpaert, Kristof Van Hecke, et al. “Asymmetric Synthesis of δ-chloro-β-amino-N-sulfinyl Imidates as Versatile Chiral Building Blocks for the Synthesis of 2,3-disubstituted Piperidines.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 22 (2015): 4847–4859. Print.
@article{6923924,
  abstract     = {Mannich-type reactions of chiral delta-chloro-N-tert-butanesulfinyl-substituted imidates across N-sulfonyl aldimines resulted in the efficient and anti-stereoselective synthesis of new beta-(sulfonylamino)-N-sulfinyl imidates (dr {\textrangle} 99:1). These compounds were then successfully cyclized to give 2-aryl-N-sulfonylpiperidine-3-(N-sulfinyl) carbimidates in high yields. These proved to be useful intermediates for the synthesis of chiral methyl 2-arylpiperidine-3-carboxylates as well as cis-3-amino-2-aryl-N-sulfonylpiperidines.},
  author       = {Semina, Elena and Colpaert, Filip and Van Hecke, Kristof and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {22},
  pages        = {4847--4859},
  title        = {Asymmetric synthesis of \ensuremath{\delta}-chloro-\ensuremath{\beta}-amino-N-sulfinyl imidates as versatile chiral building blocks for the synthesis of 2,3-disubstituted piperidines},
  url          = {http://dx.doi.org/10.1002/ejoc.201500466},
  year         = {2015},
}

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