Stereoselective Synthesis of Sex Pheromone ( R )‐4‐Methyl‐1‐Nonanol: Non‐Cross‐Linked Polystyrene Supported Oxazolidinone as a Chiral Auxiliary | Zendy

Lu Cuifen | Zendy; Li Donglai | Zendy; Wang Qiuyan | Zendy; Yang Guichun | Zendy; Chen Zuxing | Zendy

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Stereoselective Synthesis of Sex Pheromone ( R )‐4‐Methyl‐1‐Nonanol: Non‐Cross‐Linked Polystyrene Supported Oxazolidinone as a Chiral Auxiliary

Author(s) -

Lu Cuifen,

Li Donglai,

Wang Qiuyan,

Yang Guichun,

Chen Zuxing

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800758

Subject(s) - stereoselectivity , chemistry , polystyrene , enantiomer , yield (engineering) , reagent , enantiomeric excess , organic chemistry , enantioselective synthesis , stereochemistry , catalysis , polymer , materials science , metallurgy

( R )‐4‐Methyl‐1‐nonanol, the sex pheromone of the yellow mealworm ( Tenebrio Molitor L.), was synthesized by using non‐cross‐linked polystyrene supported oxazolidinone as a chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addition of an organocopper reagent to non‐cross‐linked polystyrene supported N ‐crotonoyoxazolidinone, and the target product was obtained in an overall yield of 41.8 % over seven steps with a high enantiomeric excess of 98 %.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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