TY - JOUR UR - http://lib.ugent.be/catalog/pug01:2100766 ID - pug01:2100766 LA - eng TI - 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 PY - 2012 JO - (2012) ORGANIC & BIOMOLECULAR CHEMISTRY SN - 1477-0520 PB - 2012 AU - Callebaut, Gert UGent 002004109623 802000651653 AU - Mangelinckx, Sven LA24 001996036896 801001593685 0000-0002-9349-880X AU - Kiss, Lorand AU - Sillanpaa, Reijo AU - Fulop, Ferenc AU - De Kimpe, Norbert UGent 801000520827 AB - 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. ER -Download RIS file
| 00000nam^a2200301^i^4500 | |||
| 001 | 2100766 | ||
| 005 | 20180813141430.0 | ||
| 008 | 120508s2012------------------------eng-- | ||
| 022 | a 1477-0520 | ||
| 024 | a 000300656600020 2 wos | ||
| 024 | a 1854/LU-2100766 2 handle | ||
| 024 | a 10.1039/c2ob06637h 2 doi | ||
| 040 | a UGent | ||
| 245 | a 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 | ||
| 246 | a 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 | ||
| 260 | c 2012 | ||
| 520 | a 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. | ||
| 598 | a A1 | ||
| 700 | a Callebaut, Gert u UGent 0 002004109623 0 802000651653 0 978651212051 9 0AC8883C-F0EE-11E1-A9DE-61C894A0A6B4 | ||
| 700 | a Mangelinckx, Sven u LA24 0 001996036896 0 801001593685 0 0000-0002-9349-880X 9 F65B9272-F0ED-11E1-A9DE-61C894A0A6B4 | ||
| 700 | a Kiss, Lorand | ||
| 700 | a Sillanpaa, Reijo | ||
| 700 | a Fulop, Ferenc | ||
| 700 | a De Kimpe, Norbert u UGent 0 801000520827 0 978899405446 9 F418046E-F0ED-11E1-A9DE-61C894A0A6B4 | ||
| 650 | a Chemistry | ||
| 653 | a GENERAL-METHOD | ||
| 653 | a WILLARDIINE | ||
| 653 | a ESTERS | ||
| 653 | a BIOSYNTHESIS | ||
| 653 | a SULFINIMINES | ||
| 653 | a DEPROTECTION | ||
| 653 | a CONVENIENT SYNTHESIS | ||
| 653 | a QUISQUALIC ACID | ||
| 653 | a OXALYLAMINO-L-ALANINE | ||
| 653 | a BETA-AMINO ACIDS | ||
| 773 | t ORGANIC & BIOMOLECULAR CHEMISTRY g Org. Biomol. Chem. 2012. 10 (11) p.2326-2338 q 10:11<2326 | ||
| 856 | 3 fullText u https://biblio.ugent.be/publication/2100766/file/2100774 z [UGent only] y Callebaut_Mangelinckx_-OrgBiomolChem2012-2326.pdf | ||
| 920 | a article | ||
| Z30 | x BW 1 LA11 | ||
| 922 | a UGENT-BW | ||
| 856 | 3 fullText u http://sfxit.ugent.be/sfx_local?sid=bellow&atitle=Asymmetric%20synthesis%20of%20%CE%B1%2C%CE%B2-diamino%20acid%20derivatives%20with%20an%20aziridine-%2C%20azetidine-%20and%20%CE%B3-lactone-skeleton%20via%20Mannich-type%20additions%20across%20%CE%B1-chloro-N-sulfinylimines&issn=1477-0520&volume=10&issue=11&spage=2326&date=2012&svc.fulltext=yes z [ugent] y SFX openurl | ||
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