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Aspects of stereocontrol in the L-Selectride reduction of 4-acyl-1,3-dioxolane derivatives

Abstract:
The application of L-Selectride, either alone or in combination with ZnCl2, to aryl ketones 1, 8 and 11 resulted in highly anti-stereoselective reduction. In contrast, lactols 22 and 23 gave a moderate syn-preference using L-Selectride alone and a high syn-preference in the presence of ZnCl2. Uniquely, high anti- stereoselectivity was observed in the reduction of o-anisyl lactol 37 with L-Selectride alone, which was switched to a high syn-preference when ZnCl2 was present. © 2010 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Publisher copy:
10.1016/j.tet.2010.01.107

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Unsworth, WP More by this author
Lamont, SG More by this author
Journal:
TETRAHEDRON
Volume:
66
Issue:
13
Pages:
2363-2372
Publication date:
2010-03-27
DOI:
ISSN:
0040-4020
URN:
uuid:118c78a3-5454-4c8c-9250-8f63a627dda5
Source identifiers:
55212
Local pid:
pubs:55212
Language:
English
Keywords:

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