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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

Gert Callebaut UGent, Sven Mangelinckx UGent, Lorand Kiss, Reijo Sillanpaa, Ferenc Fulop and Norbert De Kimpe UGent (2012) ORGANIC & BIOMOLECULAR CHEMISTRY. 10(11). p.2326-2338
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.
Please use this url to cite or link to this publication:
author
organization
alternative title
Asymmetric synthesis of alpha,beta-diamino acid derivatives with an aziridine-, azetidine- and gamma-lactone-skeleton via Mannich-type additions across alpha-chloro-N-sulfinylimines
year
type
journalArticle (original)
publication status
published
subject
keyword
GENERAL-METHOD, WILLARDIINE, ESTERS, BIOSYNTHESIS, SULFINIMINES, DEPROTECTION, CONVENIENT SYNTHESIS, QUISQUALIC ACID, OXALYLAMINO-L-ALANINE, BETA-AMINO ACIDS
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
10
issue
11
pages
2326 - 2338
Web of Science type
Article
Web of Science id
000300656600020
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.568 (2012)
JCR rank
11/55 (2012)
JCR quartile
1 (2012)
ISSN
1477-0520
DOI
10.1039/c2ob06637h
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
2100766
handle
http://hdl.handle.net/1854/LU-2100766
date created
2012-05-08 08:43:36
date last changed
2012-05-08 13:34:01
@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},
  keyword      = {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 \ensuremath{\alpha},\ensuremath{\beta}-diamino acid derivatives with an aziridine-, azetidine- and \ensuremath{\gamma}-lactone-skeleton via Mannich-type additions across \ensuremath{\alpha}-chloro-N-sulfinylimines},
  url          = {http://dx.doi.org/10.1039/c2ob06637h},
  volume       = {10},
  year         = {2012},
}

Chicago
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.
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.
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.
MLA
Callebaut, Gert, Sven Mangelinckx, Lorand Kiss, 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 10.11 (2012): 2326–2338. Print.