Literature DB >> 17503837

Stereoselective iodocyclization of (S)-allylalanine derivatives: gamma-lactone vs cyclic carbamate formation.

Mariella Pattarozzi1, Cristiano Zonta, Quirinus B Broxterman, Bernard Kaptein, Rita De Zorzi, Lucio Randaccio, Paolo Scrimin, Giulia Licini.   

Abstract

An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.

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Year:  2007        PMID: 17503837     DOI: 10.1021/ol070764k

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Synthesis, Radiolabeling, and Biological Evaluation of (R)- and (S)-2-Amino-5-[(18)F]fluoro-2-methylpentanoic Acid ((R)-, (S)-[(18)F]FAMPe) as Potential Positron Emission Tomography Tracers for Brain Tumors.

Authors:  Ahlem Bouhlel; Dong Zhou; Aixiao Li; Liya Yuan; Keith M Rich; Jonathan McConathy
Journal:  J Med Chem       Date:  2015-05-04       Impact factor: 7.446

2.  Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

Authors:  Brett E Howard; K A Woerpel
Journal:  Tetrahedron       Date:  2009-09-01       Impact factor: 2.457

  2 in total

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