Synthesis of chiral β-aminophosphonates via Rh-catalyzed asymmetric hydrogenation of β-amido-vinylphosphonates

Tetrahedron Asymmetry

Volumn 19, Issue 10, 2008, Pages 1189-1192

  Kadyrov, Renat ^a   Holz, Jens ^b   Schäffner, Benjamin ^b   Zayas, Odalys ^c   Almena, Juan ^a   Börner, Armin ^a,b  

^a EVONIK INDUSTRIES AG   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^c UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMIDO VINYLPHOSPHONATE DERIVATIVE; BETA AMINOPHOSPHONATE DERIVATIVE; BETA N ACETYLAMINO PHOSPHONATE DERIVATIVE; BETA N ACETYLAMINO VINYLPHOSPHONATE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RHODIUM;

ACETYLATION; ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 44649125366     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.04.019     Document Type: Article

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49. All results of the HTS can be obtained from the authors on request.
50. 4 in methanol, the chiral product was obtained in quantitative yield and in 94% ee. Obviously in some cases the HTS-approach can give some misleading results. Currently, this aspect is under investigation.
51. Up to now correlation of the sign of the specific rotation with the absolute configuration cannot be given. A comparison with the specific rotation of known chiral β-substituted β-amino-ethan-1-ylphosphonates indicates that a positive sign correlates with an (S)-configuration.