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Asymmetric synthesis of alpha-Chloro-beta-amino-N-sulfinyl imidates as chiral building blocks

Filip Colpaert (UGent) , Sven Mangelinckx (UGent) , Stijn De Brabandere (UGent) and Norbert De Kimpe (UGent)
(2011) JOURNAL OF ORGANIC CHEMISTRY. 76(7). p.2204-2213
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Abstract
New chiral alpha-chloro-beta-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (R-S)-methyl N-tert-butanesulfinyl-2-chloroethanimidate with aromatic aldimines. The alpha-chloro-beta-amino-N-sulfinylimidates proved to be excellent building blocks for the asymmetric synthesis of beta-amino-alpha-chloro amides and esters, aziridine-2-carboxylic amides and esters, trans-2-aryl-3-chloroazetidines, and methyl 4-phenyloxazolidin-2-one-5-carboxylate. The obtained absolute anti-diastereoselectivity is the opposite of the stereochemical outcome observed for alpha-methyl-substituted imidates.
Keywords
MANNICH-TYPE REACTIONS, RING-OPENING REACTIONS, ACID-DERIVATIVES, NITRILE BIOTRANSFORMATIONS, STEREOSELECTIVE-SYNTHESIS, AQUEOUS-SOLUTION, IMINES, AZIRIDINES, SULFINIMINES, EFFICIENT

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MLA
Colpaert, Filip, Sven Mangelinckx, Stijn De Brabandere, et al. “Asymmetric Synthesis of alpha-Chloro-beta-amino-N-sulfinyl Imidates as Chiral Building Blocks.” JOURNAL OF ORGANIC CHEMISTRY 76.7 (2011): 2204–2213. Print.
APA
Colpaert, F., Mangelinckx, S., De Brabandere, S., & De Kimpe, N. (2011). Asymmetric synthesis of alpha-Chloro-beta-amino-N-sulfinyl imidates as chiral building blocks. JOURNAL OF ORGANIC CHEMISTRY, 76(7), 2204–2213.
Chicago author-date
Colpaert, Filip, Sven Mangelinckx, Stijn De Brabandere, and Norbert De Kimpe. 2011. “Asymmetric Synthesis of alpha-Chloro-beta-amino-N-sulfinyl Imidates as Chiral Building Blocks.” Journal of Organic Chemistry 76 (7): 2204–2213.
Chicago author-date (all authors)
Colpaert, Filip, Sven Mangelinckx, Stijn De Brabandere, and Norbert De Kimpe. 2011. “Asymmetric Synthesis of alpha-Chloro-beta-amino-N-sulfinyl Imidates as Chiral Building Blocks.” Journal of Organic Chemistry 76 (7): 2204–2213.
Vancouver
1.
Colpaert F, Mangelinckx S, De Brabandere S, De Kimpe N. Asymmetric synthesis of alpha-Chloro-beta-amino-N-sulfinyl imidates as chiral building blocks. JOURNAL OF ORGANIC CHEMISTRY. 2011;76(7):2204–13.
IEEE
[1]
F. Colpaert, S. Mangelinckx, S. De Brabandere, and N. De Kimpe, “Asymmetric synthesis of alpha-Chloro-beta-amino-N-sulfinyl imidates as chiral building blocks,” JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 7, pp. 2204–2213, 2011.
@article{1205859,
  abstract     = {New chiral alpha-chloro-beta-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (R-S)-methyl N-tert-butanesulfinyl-2-chloroethanimidate with aromatic aldimines. The alpha-chloro-beta-amino-N-sulfinylimidates proved to be excellent building blocks for the asymmetric synthesis of beta-amino-alpha-chloro amides and esters, aziridine-2-carboxylic amides and esters, trans-2-aryl-3-chloroazetidines, and methyl 4-phenyloxazolidin-2-one-5-carboxylate. The obtained absolute anti-diastereoselectivity is the opposite of the stereochemical outcome observed for alpha-methyl-substituted imidates.},
  author       = {Colpaert, Filip and Mangelinckx, Sven and De Brabandere, Stijn and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {MANNICH-TYPE REACTIONS,RING-OPENING REACTIONS,ACID-DERIVATIVES,NITRILE BIOTRANSFORMATIONS,STEREOSELECTIVE-SYNTHESIS,AQUEOUS-SOLUTION,IMINES,AZIRIDINES,SULFINIMINES,EFFICIENT},
  language     = {eng},
  number       = {7},
  pages        = {2204--2213},
  title        = {Asymmetric synthesis of alpha-Chloro-beta-amino-N-sulfinyl imidates as chiral building blocks},
  url          = {http://dx.doi.org/10.1021/jo200082w},
  volume       = {76},
  year         = {2011},
}

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