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The asymmetric hydroformylation in the synthesis of pharmaceuticals
Author(s) -
Botteghi Carlo,
Paganelli Stefano,
Schionato Alberto,
Marchetti Mauro
Publication year - 1991
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530030422
Subject(s) - hydroformylation , chemistry , synthon , enantioselective synthesis , enantiomer , combinatorial chemistry , rhodium , optically active , catalysis , organic chemistry , chelation , stereochemistry
The asymmetric hydroformylation reaction represents a potential powerful synthetic tool for the preparation of large number of different chiral products to be used as precursors of several organic compounds endowed with therapeutic activity. Essential and nonessential amino acids, 2‐arylpropanoic acids, aryloxypropyl‐ and β‐phenylpropylamines, modified β‐phenylethylamines, pheniramines, and other classes of pharmaceuticals are available through enantioselective oxo ‐reaction of appropriate functionalized olefins; this process is catalyzed by rhodium or platinum complexes with chiral ligands, mainly chelating phosphines, and sometimes affords very high enantiomeric excesses. Furthermore, the application of many simple optically active aldehydes arising from asymmetric hydroformylation as chiral building blocks for the synthesis of complex pharmacologically active molecules such as antibiotics, peptides, antitumor macrocycle compounds, and prostaglandins is conveniently emphasized. The possibility of a future application of this asymmetric process for the production of many synthons to obtain other valuable pharmaceuticals is widely discussed too.