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Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines

(2014) ORGANIC & BIOMOLECULAR CHEMISTRY. 12(21). p.3393-3405
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Abstract
Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-alpha-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new gamma-chloro-alpha-hydroxy-beta-amino esters (dr > 99 : 1). The alpha-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the lithium ion of the incoming E-enolate in the transition state model. These novel chloroisothreonine derivatives proved to be excellent building blocks in asymmetric synthesis of novel syn-beta,gamma-aziridino-alpha-hydroxyesters and biologically relevant trans-oxazolidinone carboxylic esters.
Keywords
PEPTIDASE-II INHIBITORS, ENANTIOSELECTIVE SYNTHESIS, BETA-AMINO ACIDS, TERT-BUTANESULFINYL IMINES, DIASTEREOSELECTIVE SYNTHESIS, MEDICINAL CHEMISTRY, SIDE-CHAIN, AZIRIDINES, ANALOGS, POTENT

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Chicago
Callebaut, Gert, Filip Colpaert, Melinda Nonn, Loránd Kiss, Reijo Sillanpää, Karl W Törnroos, Ferenc Fülöp, Norbert De Kimpe, and Sven Mangelinckx. 2014. “Asymmetric Synthesis of Chloroisothreonine Derivatives via Syn-stereoselective Mannich-type Additions Across N-sulfinyl-α-chloroimines.” Organic & Biomolecular Chemistry 12 (21): 3393–3405.
APA
Callebaut, G., Colpaert, F., Nonn, M., Kiss, L., Sillanpää, R., Törnroos, K. W., Fülöp, F., et al. (2014). Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines. ORGANIC & BIOMOLECULAR CHEMISTRY, 12(21), 3393–3405.
Vancouver
1.
Callebaut G, Colpaert F, Nonn M, Kiss L, Sillanpää R, Törnroos KW, et al. Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines. ORGANIC & BIOMOLECULAR CHEMISTRY. 2014;12(21):3393–405.
MLA
Callebaut, Gert, Filip Colpaert, Melinda Nonn, et al. “Asymmetric Synthesis of Chloroisothreonine Derivatives via Syn-stereoselective Mannich-type Additions Across N-sulfinyl-α-chloroimines.” ORGANIC & BIOMOLECULAR CHEMISTRY 12.21 (2014): 3393–3405. Print.
@article{4413161,
  abstract     = {Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-alpha-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new gamma-chloro-alpha-hydroxy-beta-amino esters (dr {\textrangle} 99 : 1). The alpha-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the lithium ion of the incoming E-enolate in the transition state model. These novel chloroisothreonine derivatives proved to be excellent building blocks in asymmetric synthesis of novel syn-beta,gamma-aziridino-alpha-hydroxyesters and biologically relevant trans-oxazolidinone carboxylic esters.},
  author       = {Callebaut, Gert and Colpaert, Filip and Nonn, Melinda and Kiss, Lor{\'a}nd and Sillanp{\"a}{\"a}, Reijo and T{\"o}rnroos, Karl W and F{\"u}l{\"o}p, Ferenc and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  language     = {eng},
  number       = {21},
  pages        = {3393--3405},
  title        = {Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-\ensuremath{\alpha}-chloroimines},
  url          = {http://dx.doi.org/10.1039/c4ob00243a},
  volume       = {12},
  year         = {2014},
}

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