An alternative stereoselective synthesis of ( R )‐ and ( S )‐Rosaphen® via asymmetric  catalytic hydrogenation | Zendy

Matteoli Ugo | Zendy; Beghetto Valentina | Zendy; Scrivanti Alberto | Zendy; Aversa Manuela | Zendy; Bertoldini Matteo | Zendy; Bovo Sara | Zendy

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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.

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