Asymmetric synthesis of alpha-Chloro-beta-amino-N-sulfinyl imidates as chiral building blocks
- Author
- Filip Colpaert (UGent) , Sven Mangelinckx (UGent) , Stijn De Brabandere (UGent) and Norbert De Kimpe (UGent)
- Organization
- 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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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-1205859
- MLA
- Colpaert, Filip, et al. “Asymmetric Synthesis of Alpha-Chloro-Beta-Amino-N-Sulfinyl Imidates as Chiral Building Blocks.” JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 7, 2011, pp. 2204–13, doi:10.1021/jo200082w.
- 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. https://doi.org/10.1021/jo200082w
- 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): 2204–13. https://doi.org/10.1021/jo200082w.
- 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. doi:10.1021/jo200082w.
- 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://doi.org/10.1021/jo200082w}},
volume = {{76}},
year = {{2011}},
}
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