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

Callebaut, Gert and Colpaert, Filip and Nonn, Melinda and Kiss, Loránd and Sillanpa, Rejo and Törnroos, Karl W. and Fülöp, Ferenc and De Kimpe, Norbert and Mangelinckx, Sven (2014) Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines. Organic and Biomolecular Chemistry, 12. pp. 3393-3405. ISSN 1477-0520, ESSN: 1477-0539

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Abstract

Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-α-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new γ-chloro-α-hydroxy-β-amino esters (dr > 99 : 1). The α-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-β,γ-aziridino-α-hydroxy esters and biologically relevant trans-oxazolidinone carboxylic esters

Item Type:	Article
Subjects:	Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User:	Dr Loránd Kiss
Date Deposited:	11 Sep 2014 12:23
Last Modified:	12 Sep 2014 08:13
URI:	http://real.mtak.hu/id/eprint/14724

Available Versions of this Item

• Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines. (deposited 09 Sep 2014 13:40)
  • Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines. (deposited 11 Sep 2014 12:23) [Currently Displayed]

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