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A stereoselective oxy-Michael approach to THP*-protected beta-hydroxy esters

Abstract:
The 'naked' anion of (S)-6-methyl δ-lactol undergoes efficient oxy-Michael addition to α,β-unsaturated methyl sulfones to give the corresponding adducts with excellent (up to 99% de) stereocontrol at the newly formed stereogenic β-centre. The successive reductive desulfonylation using excess samarium(II) iodide under mild reaction conditions affords the THP*protected β-hydroxy esters as single diastereoisomers after chromatography on silica gel. © Georg Thieme Verlag Stuttgart.
Publication status:
Published

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Publisher copy:
10.1055/s-2005-918484

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
SYNTHESIS-STUTTGART
Issue:
19
Pages:
3283-3286
Publication date:
2005-12-01
DOI:
EISSN:
1437-210X
ISSN:
0039-7881
URN:
uuid:ff3afc4e-84cc-434a-82dd-9285a7e8c200
Source identifiers:
39752
Local pid:
pubs:39752

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