Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines
- Author
- Filip Colpaert (UGent) , Sven Mangelinckx (UGent) and Norbert De Kimpe (UGent)
- Organization
- Abstract
- New chiral beta-(sulfonylamino)sulfinylimidates are synthesized in high overall yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of chiral N-tert-butanesulfinyl imidates with N-tosyl aldimines. Deprotection of the beta-(sulfonylamino)sulfinylimidates gave access to enantiopure imidate hydrochlorides in high yields, as useful intermediates for an easy transformation to new chiral beta-sulfonylamino amides upon simple heating in chloroform. Hydrolysis of the imidate hydrochlorides afforded the corresponding chiral beta-sulfonylamino esters with >98% ee as new chiral beta-amino acid derivatives.
- Keywords
- CATALYTIC ADDITION, SULFINIMINES, 3-AMINO ALCOHOLS, ADDITION-REACTIONS, ANTI-1, SYN-1, 3-AMINO, DESIGN, ESTER, ANALOGS, ACTIVATED IMINES
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-944962
- MLA
- Colpaert, Filip, et al. “Asymmetric Synthesis of New Chiral β-Amino Acid Derivatives by Mannich-Type Reactions of Chiral N-Sulfinyl Imidates with N-Tosyl Aldimines.” ORGANIC LETTERS, vol. 12, no. 9, 2010, pp. 1904–07, doi:10.1021/ol100073y.
- APA
- Colpaert, F., Mangelinckx, S., & De Kimpe, N. (2010). Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines. ORGANIC LETTERS, 12(9), 1904–1907. https://doi.org/10.1021/ol100073y
- Chicago author-date
- Colpaert, Filip, Sven Mangelinckx, and Norbert De Kimpe. 2010. “Asymmetric Synthesis of New Chiral β-Amino Acid Derivatives by Mannich-Type Reactions of Chiral N-Sulfinyl Imidates with N-Tosyl Aldimines.” ORGANIC LETTERS 12 (9): 1904–7. https://doi.org/10.1021/ol100073y.
- Chicago author-date (all authors)
- Colpaert, Filip, Sven Mangelinckx, and Norbert De Kimpe. 2010. “Asymmetric Synthesis of New Chiral β-Amino Acid Derivatives by Mannich-Type Reactions of Chiral N-Sulfinyl Imidates with N-Tosyl Aldimines.” ORGANIC LETTERS 12 (9): 1904–1907. doi:10.1021/ol100073y.
- Vancouver
- 1.Colpaert F, Mangelinckx S, De Kimpe N. Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines. ORGANIC LETTERS. 2010;12(9):1904–7.
- IEEE
- [1]F. Colpaert, S. Mangelinckx, and N. De Kimpe, “Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines,” ORGANIC LETTERS, vol. 12, no. 9, pp. 1904–1907, 2010.
@article{944962,
abstract = {{New chiral beta-(sulfonylamino)sulfinylimidates are synthesized in high overall yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of chiral N-tert-butanesulfinyl imidates with N-tosyl aldimines. Deprotection of the beta-(sulfonylamino)sulfinylimidates gave access to enantiopure imidate hydrochlorides in high yields, as useful intermediates for an easy transformation to new chiral beta-sulfonylamino amides upon simple heating in chloroform. Hydrolysis of the imidate hydrochlorides afforded the corresponding chiral beta-sulfonylamino esters with >98% ee as new chiral beta-amino acid derivatives.}},
author = {{Colpaert, Filip and Mangelinckx, Sven and De Kimpe, Norbert}},
issn = {{1523-7060}},
journal = {{ORGANIC LETTERS}},
keywords = {{CATALYTIC ADDITION,SULFINIMINES,3-AMINO ALCOHOLS,ADDITION-REACTIONS,ANTI-1,SYN-1,3-AMINO,DESIGN,ESTER,ANALOGS,ACTIVATED IMINES}},
language = {{eng}},
number = {{9}},
pages = {{1904--1907}},
title = {{Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines}},
url = {{http://doi.org/10.1021/ol100073y}},
volume = {{12}},
year = {{2010}},
}
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