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An alternative stereoselective synthesis of ( R )‐ and ( S )‐Rosaphen® via asymmetric catalytic hydrogenation
Author(s) -
Matteoli Ugo,
Beghetto Valentina,
Scrivanti Alberto,
Aversa Manuela,
Bertoldini Matteo,
Bovo Sara
Publication year - 2011
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.20989
Subject(s) - chemistry , stereoselectivity , asymmetric hydrogenation , chirality (physics) , catalysis , phosphine , ruthenium , enantiomer , enantioselective synthesis , stereochemistry , organic chemistry , combinatorial chemistry , chiral symmetry , physics , quantum mechanics , quark , nambu–jona lasinio model
We report an alternative synthesis of the two enantiomers of the floral fragrance Rosaphen®. The key intermediate 2‐methyl‐5‐phenylpentanoic acid 3 is synthesized via asymmetric hydrogenation ( ee up to 99%) in the presence of an in situ prepared ruthenium catalyst containing the chiral ferrocenyl phosphine Mandyphos‐4. Chirality, 2011. © 2011 Wiley‐Liss, Inc.