Journal
TETRAHEDRON LETTERS
Volume 50, Issue 38, Pages 5305-5307Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.06.136
Keywords
Asymmetric synthesis; Conjugate addition; Allylation; Ring-closing metathesis; Spirocyclic ether
Categories
Funding
- Academy of Finland [203283]
- Graduate School of Organic Chemistry and Chemical Biology
- Academy of Finland (AKA) [203283, 203283] Funding Source: Academy of Finland (AKA)
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The preparation of chiral spirocyclic ethers via allylic etherification/olefin metathesis of homoallylic alcohols is investigated. This reaction sequence transforms the enantiopure substrate alcohols, synthesized by a one-pot asymmetric rhodium-catalyzed conjugate addition/metal-mediated allylation procedure, into the desired spite ethers with full conversions and in excellent isolated yields. The synthetic sequence provides an efficient means for a rapid construction of functionalized spiro ethers in a stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.
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