Ring-closing metathesis as a tool for the efficient preparation of chiral spirocyclic ethers from homoallylic alcohols

Tetrahedron Letters

Volumn 50, Issue 38, 2009, Pages 5305-5307

  Rosenberg, Sara ^a   Leino, Reko ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

Author keywords

Allylation; Asymmetric synthesis; Conjugate addition; Ring closing metathesis; Spirocyclic ether

Indexed keywords

ALLYL ALCOHOL; ETHER DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ETHERIFICATION; RING CLOSING METATHESIS;

EID: 68049109369     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.136     Document Type: Article

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23. 2 (0.3 mL) was prepared. The solution of 2a was cooled in an ice bath and treated dropwise with the solution of catalyst over approximately 5 min. The reaction mixture was then removed from the ice bath, allowed to warm to rt and stirred overnight. After 12 h, the reaction product was purified by flash chromatography by passing the reaction mixture, as such, through a silica gel column affording 3a (28.7 mg, 90% from 1a) as a light yellow oil. For analytical data, see Supplementary data.
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