Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with Grignard reagents

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3734-3736

  Zhang, Wei ^a   Wang, Li Xin ^a   Shi, Wen Jian ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSIS; CATALYST SELECTIVITY; COPPER; REACTION KINETICS;

ASYMMETRIC RING OPENING; ENANTIOSELECTIVITY; GRIGNARD REAGENTS; STEROSELECTIVITY;

OLEFINS;

ALKADIENE; ALKENE DERIVATIVE; COPPER; GRIGNARD REAGENT; LIGAND; OXABENZONORBORNADIENE DERIVATIVE; PHOSPHORAMIDOUS ACID; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; RING OPENING; STEREOCHEMISTRY;

EID: 17744387945     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050015l     Document Type: Article

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31. The Grignard reagents used in this paper are as ether solutions. The ether concentration in the reaction solution is around 10% in volume, which is important for keeping the reaction homogeneous. Reducing the ether concentration led to a precipitation of Grignard reagents and resulted in a lower yield and lower selectivity.
32. The minor syn-adducts obtained in all reactions throughout this work were racemic. The side product 1,2-dihydronaphthalen-1-ol (<2%) was detected.
33. a,S,S)-Monophos-PE gave comparable enantioselectivities. They produced the alkylated ring-opening product 2a in 51% yield in 93:7 anti/syn ratio with 51% ee and 38% yield in 98:2 anti/syn ratio with 47% ee, respectively.
34. The 7-oxabenzonorbornadienes could not be completely converted in the coordinating solvents.