Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines
- Author
- Gert Callebaut (UGent) , Sven Mangelinckx (UGent) , Lorand Kiss, Reijo Sillanpaa, Ferenc Fulop and Norbert De Kimpe (UGent)
- Organization
- Abstract
- The efficient asymmetric synthesis of new chiral gamma-chloro-alpha,beta-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral alpha-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity of the Mannich-type reaction. The gamma-chloro-alpha,beta-diamino acid derivatives proved to be excellent building blocks for ring closure towards optically pure anti-and syn-beta,gamma-aziridino-alpha-amino esters, and subsequent ring transformation into trans-3-aminoazetidine-2-carboxylic acid derivatives and alpha,beta-diamino-gamma-butyrolactones.
- Keywords
- GENERAL-METHOD, WILLARDIINE, ESTERS, BIOSYNTHESIS, SULFINIMINES, DEPROTECTION, CONVENIENT SYNTHESIS, QUISQUALIC ACID, OXALYLAMINO-L-ALANINE, BETA-AMINO ACIDS
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-2100766
- MLA
- Callebaut, Gert, et al. “Asymmetric Synthesis of α,β-Diamino Acid Derivatives with an Aziridine-, Azetidine- and γ-Lactone-Skeleton via Mannich-Type Additions across α-Chloro-N-Sulfinylimines.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 11, 2012, pp. 2326–38, doi:10.1039/c2ob06637h.
- APA
- Callebaut, G., Mangelinckx, S., Kiss, L., Sillanpaa, R., Fulop, F., & De Kimpe, N. (2012). Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines. ORGANIC & BIOMOLECULAR CHEMISTRY, 10(11), 2326–2338. https://doi.org/10.1039/c2ob06637h
- Chicago author-date
- Callebaut, Gert, Sven Mangelinckx, Lorand Kiss, Reijo Sillanpaa, Ferenc Fulop, and Norbert De Kimpe. 2012. “Asymmetric Synthesis of α,β-Diamino Acid Derivatives with an Aziridine-, Azetidine- and γ-Lactone-Skeleton via Mannich-Type Additions across α-Chloro-N-Sulfinylimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 10 (11): 2326–38. https://doi.org/10.1039/c2ob06637h.
- Chicago author-date (all authors)
- Callebaut, Gert, Sven Mangelinckx, Lorand Kiss, Reijo Sillanpaa, Ferenc Fulop, and Norbert De Kimpe. 2012. “Asymmetric Synthesis of α,β-Diamino Acid Derivatives with an Aziridine-, Azetidine- and γ-Lactone-Skeleton via Mannich-Type Additions across α-Chloro-N-Sulfinylimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 10 (11): 2326–2338. doi:10.1039/c2ob06637h.
- Vancouver
- 1.Callebaut G, Mangelinckx S, Kiss L, Sillanpaa R, Fulop F, De Kimpe N. Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines. ORGANIC & BIOMOLECULAR CHEMISTRY. 2012;10(11):2326–38.
- IEEE
- [1]G. Callebaut, S. Mangelinckx, L. Kiss, R. Sillanpaa, F. Fulop, and N. De Kimpe, “Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 11, pp. 2326–2338, 2012.
@article{2100766,
abstract = {{The efficient asymmetric synthesis of new chiral gamma-chloro-alpha,beta-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral alpha-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity of the Mannich-type reaction. The gamma-chloro-alpha,beta-diamino acid derivatives proved to be excellent building blocks for ring closure towards optically pure anti-and syn-beta,gamma-aziridino-alpha-amino esters, and subsequent ring transformation into trans-3-aminoazetidine-2-carboxylic acid derivatives and alpha,beta-diamino-gamma-butyrolactones.}},
author = {{Callebaut, Gert and Mangelinckx, Sven and Kiss, Lorand and Sillanpaa, Reijo and Fulop, Ferenc and De Kimpe, Norbert}},
issn = {{1477-0520}},
journal = {{ORGANIC & BIOMOLECULAR CHEMISTRY}},
keywords = {{GENERAL-METHOD,WILLARDIINE,ESTERS,BIOSYNTHESIS,SULFINIMINES,DEPROTECTION,CONVENIENT SYNTHESIS,QUISQUALIC ACID,OXALYLAMINO-L-ALANINE,BETA-AMINO ACIDS}},
language = {{eng}},
number = {{11}},
pages = {{2326--2338}},
title = {{Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines}},
url = {{http://doi.org/10.1039/c2ob06637h}},
volume = {{10}},
year = {{2012}},
}
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