Control of Chemo‑, Regio‑, and Enantioselectivity in Copper Hydride Reductions of Morita–Baylis–Hillman Adducts
Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita–Baylis–Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those with β-substitution, can be transformed to stereodefined...
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Published in | Organic letters Vol. 19; no. 2; pp. 328 - 331 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
20.01.2017
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita–Baylis–Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those with β-substitution, can be transformed to stereodefined enoates by taking advantage of a bulky, oligomeric, in situ generated trialkoxysiloxane leaving group. Finally, an atypical conversion of easily arrived at MBH alcohol derivatives to nonracemic allylic alcohols is disclosed. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.6b03464 |